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1. 发明授权

US5194628A Process for the preparation of substituted difluorobenzo-1,3-dioxoles 失效
标题翻译：制备取代的二氟苯-1,3-二氧杂环戊烯的方法
公开(公告)号：US5194628A
公开(公告)日：1993-03-16
申请号：US583787
申请日：1990-09-14
申请人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
发明人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
IPC分类号： C07D317/46 , C07D405/04 , C07F1/00 , C07F1/02 , C07F3/00 , C07F5/02 , C07F7/08 , C07F7/10 , C07F19/00
CPC分类号： C07D405/04 , C07D317/46 , C07F1/00 , C07F1/02 , C07F19/00 , C07F3/00 , C07F5/025 , C07F7/0814 , C07F7/10 , Y02P20/55
摘要： The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 l in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 l is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkyl, nitro or by cyano, or is C.sub.1 -C.sub.12 acyl, or wherein R.sup. 1 is a radical of formula II ##STR2## wherein R.sup.5 is --CN, --CF.sub.3, --COOR.sup.2, --CO--NHR.sup.2 or --CONR.sub.2.sup.2, R.sup.3 and R.sup.4 are a direct bond or each is H, or R.sup.3 is H and R.sup.4 independently has the meanings of R.sup.5, or R.sup.3 and R.sup.4 together are --CH.sub.2 --NR.sup.6 --CH.sub.2 --, --CH.sub.2 --NR.sup.6 --CO-- or --CO--NR.sup.6 --CO-- wherein R.sup.6 is the radical of a removable protecting group, or wherein further R.sup.1 is a radical of formula III ##STR3## Insecticides or fungicides can be prepared from the compounds of formula I. 3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole can be prepared by reacting 4-metallo-2,2-difluorobenzodioxole (III) with an unsaturated nitrile and then with a sulfonylmethyl isocyanide in a one-pot process. The compounds III are novel intermediates.
摘要翻译： 2,2-二氟苯-1,3-二氧杂环戊烯与（a）碱金属或碱金属化合物反应，然后（b）其中Z1是离去基团或与醛产生的化合物R1-Z1 式I的化合物其中R 1是-OH，-SH，-CHO，-CN，-COOH，-B（OH）2，-COX，X是Cl或Br，或是-COOR 2 ，-SiR 32或-B（OR 2）2，其中R 2是没有羟基的C 1 -C 12醇部分，其中R 1还是-C n H 2n NOR 2，n是1至4的整数，或直链或支链C 1 -C 12羟烷基，其是或者被-F，-CN，C 1 -C 6烷氧基，苯基，氟苯基，C 1 -C 4烷氧基 - 苯基，C 1 -C 4烷硫基 - 苯基，C 1 -C 4烷基 - 苯基，C 1 -C 4氟烷基 - 苯基，硝基苯基或氰基苯基取代，或其中 R1是未被取代或被F，C 1 -C 4烷氧基，C 1 -C 4烷硫基，C 1 -C 4烷基，C 1 -C 4氟烷基，硝基或氰基取代的苯甲醇，或者是C 1 -C 12酰基，或其中R 1是式 II（II）其中R5是-CN，-CF3，-COOR2，-CO-NHR2 或-CONR 22，R 3和R 4是直接键或各自为H或R 3为H且R 4独立地具有R 5的含义，或者R 3和R 4一起为-CH 2 -NR 6 -CH 2 - ， - CH 2 -NR 6 -CO- 或-CO-NR6-CO-，其中R6是可除去的保护基团的基团，或其中R1是式III的基团。（III）杀虫剂或杀真菌剂可以由式I化合物制备。（2,2-二氟苯并二氧杂环戊烯-4-基）-4-氰基吡咯可以通过4-金属-2,2-二氟苯并间二氧杂环戊烯（III）与不饱和腈然后与磺酰基甲基异氰化物在一锅法中反应来制备。化合物III是新的中间体。

2. 发明授权

US5420301A Process for the preparation of substituted difluorobenzo-1,3-dioxoles 失效
标题翻译：制备取代的二氟苯-1,3-二氧杂环戊烯的方法
公开(公告)号：US5420301A
公开(公告)日：1995-05-30
申请号：US147617
申请日：1993-11-05
申请人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
发明人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
IPC分类号： A61K31/33 , C07D317/06 , C07D317/46 , C07D405/04 , C07F1/00 , C07F1/02 , C07F3/00 , C07F5/02 , C07F7/08 , C07F7/10 , C07F19/00 , C07D317/50 , C07D317/52 , C07D317/54
CPC分类号： C07D405/04 , C07D317/46 , C07F1/00 , C07F1/02 , C07F19/00 , C07F3/00 , C07F5/025 , C07F7/0814 , C07F7/10 , Y02P20/55
摘要： The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkyl, nitro or by cyano, or is C.sub.1 -C.sub.12 acyl, or wherein R.sup.1 is a radical of formula II ##STR2## wherein R.sup.5 is --CN, --CF.sub.3, --COOR.sup.2, --CONH.sup.2, --CO--NHR.sup.2 or --CONR.sub.2.sup.2, R.sup.3 and R.sup.4 are a direct bond or each is H, or R.sup.3 is H and R.sup.4 independently has the meanings of R.sup.5, or R.sup.3 and R.sup.4 together are --CH.sub.2 --NR.sup.6 --CH.sub.2 --, --CH.sub.2 --NR.sup.6 --CO-- or --CO--NR.sup.6 --CO-- wherein R.sup.6 is the radical of a removable protecting group, or wherein further R.sup.1 is a radical of formula III ##STR3## Insecticides or fungicides can be prepared from the compounds of formula I.3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole can be prepared by reacting 4-metallo-2,2-difluorobenzodioxole (III) with an unsaturated nitrile and then with a sulfonylmethyl isocyanide in a one-pot process. The compounds III are novel intermediates.
摘要翻译： 2,2-二氟苯-1,3-二氧杂环戊烯与（a）碱金属或碱金属化合物反应，然后（b）其中Z 1为离去基团的化合物R1-Z1或与醛反应生成化合物其中R 1是-OH，-SH，-CHO，-CN，-COOH，-B（OH）2，-COX，X是Cl或Br，或者是-COOR 2， - SiR 32或-B（OR 2）2，其中R 2是没有羟基的C 1 -C 12醇部分，其中R 1还是-C n H 2n NOR 2，n是1至4的整数，或未被取代的直链或支链C 1 -C 12羟基烷基被-F，-CN，C 1 -C 6烷氧基，苯基，氟苯基，C 1 -C 4烷氧基 - 苯基，C 1 -C 4烷硫基 - 苯基，C 1 -C 4烷基 - 苯基，C 1 -C 4氟烷基 - 苯基，硝基苯基或氰基苯基取代，或其中R 1为苄基醇，其未被取代或被F，C 1 -C 4烷氧基，C 1 -C 4烷硫基，C 1 -C 4烷基，C 1 -C 4氟烷基，硝基或氰基取代，或者是C 1 -C 12酰基，或其中R 1是式II基团。（II）其中R5是-CN，-CF3，-COOR2，-CONH2，-CO-NHR 2或-CONR 22，R 3和R 4是直接键或各自为H或R 3为H且R 4独立地具有R 5的含义，或者R 3和R 4一起为-CH 2 -NR 6 -CH 2 - ， - CH 2 -NR 6 -CO - 或-CO-NR 6 -CO-，其中R 6是可除去的保护基的基团，或其中R 1是式III的基团由式I化合物制备。3-（2,2-二氟苯并二氧杂环戊烯-4-基） 4-氰基吡咯可以通过4-金属-2,2-二氟苯并二氧杂环戊烯（III）与不饱和腈然后与一种磺酰基甲基异氰化物反应来制备。化合物III是新的中间体。

3. 发明授权

US5514816A Process for the preparation of substituted difluorobenzo-1,3-dioxoles 失效
标题翻译：制备取代的二氟苯-1,3-二氧杂环戊烯的方法
公开(公告)号：US5514816A
公开(公告)日：1996-05-07
申请号：US440172
申请日：1995-05-12
申请人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
发明人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
IPC分类号： A61K31/33 , C07D317/06 , C07D317/46 , C07D405/04 , C07F1/00 , C07F1/02 , C07F3/00 , C07F5/02 , C07F7/08 , C07F7/10 , C07F19/00
CPC分类号： C07D405/04 , C07D317/46 , C07F1/00 , C07F1/02 , C07F19/00 , C07F3/00 , C07F5/025 , C07F7/0814 , C07F7/10 , Y02P20/55
摘要： The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being C1 or Br, or is --COOR.sup.2, --SiR.sup.2.sub.3 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkyl, nitro or by cyano, or is C.sub.1 -C.sub.12 acyl, or wherein R.sup.1 is a radical of formula II ##STR2## wherein R.sup.5 is --CN, --CF.sub.3, --COOR.sup.2, --CONH.sup.2, --CO--NHR.sup.2 or --CONR.sup.2.sub.2, R.sup.3 and R.sup.4 are a direct bond or each is H, or R.sup.3 is H and R.sup.4 independently has the meanings of R.sup.5, or R.sup.3 and R.sup.4 together are --CH.sub.2 --NR.sup.6 --CH.sub.2 --, --CH.sub.2 --NR.sup.6 --CO-- or --CO--NR.sup.6 --CO-- wherein R.sup.6 is the radical of a removable protecting group, or wherein further R.sup.1 is a radical of formula III ##STR3## Insecticides or fungicides can be prepared from the compounds of formula I.
摘要翻译： 2,2-二氟苯-1,3-二氧杂环戊烯与（a）碱金属或碱金属化合物反应，然后（b）其中Z 1为离去基团的化合物R1-Z1或与醛反应生成化合物其中R 1是-OH，-SH，-CHO，-CN，-COOH，-B（OH）2，-COX，X是C1或Br，或是-COOR2， - SiR 23或-B（OR 2）2，其中R 2是没有羟基的C 1 -C 12醇部分，其中R 1还是-C n H 2n COOR 2，n是1至4的整数，或未被取代的直链或支链C 1 -C 12羟基烷基或被-F，-CN，C 1 -C 6烷氧基，苯基，氟苯基，C 1 -C 4烷氧基 - 苯基，C 1 -C 4烷硫基 - 苯基，C 1 -C 4烷基苯基，C 1 -C 4氟烷基 - 苯基，硝基苯基或氰基苯基取代，或其中R 1是未被取代或被F，C 1 -C 4烷氧基，C 1 -C 4烷硫基，C 1 -C 4烷基，C 1 -C 4氟烷基，硝基或氰基取代的苯甲醇，或者是C 1 -C 12酰基，或其中R 1是式II基团 -CONH 2，-CO-NHR 2或-CONR 22，R 3和R 4是直接键或各自为H或R 3为H且R 4独立地具有R 5的含义，或者R 3和R 4一起为-CH 2 -NR 6 -CH 2 - ， - CH 2 -NR 6 -CO-或-CO-NR 6 -CO-，其中R 6为可除去的保护基团的基团，或其中R 1为式III的基团。（III）杀虫剂或杀真菌剂可由式I化合物制备。

4. 发明授权

US5493032A Process for the preparation of substituted difluorobenzo-1,3-dioxoles 失效
标题翻译：制备取代的二氟苯-1,3-二氧杂环戊烯的方法
公开(公告)号：US5493032A
公开(公告)日：1996-02-20
申请号：US399248
申请日：1995-03-06
申请人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
发明人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
IPC分类号： A61K31/33 , C07D317/06 , C07D317/46 , C07D405/04 , C07F1/00 , C07F1/02 , C07F3/00 , C07F5/02 , C07F7/08 , C07F7/10 , C07F19/00
CPC分类号： C07D405/04 , C07D317/46 , C07F1/00 , C07F1/02 , C07F19/00 , C07F3/00 , C07F5/025 , C07F7/0814 , C07F7/10 , Y02P20/55
摘要： The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1##
摘要翻译： 2,2-二氟苯-1,3-二氧杂环戊烯与（a）碱金属或碱金属化合物反应，然后（b）其中Z 1为离去基团的化合物R1-Z1或与醛反应生成化合物式I（I）

5. 发明授权

US5281718A Process for the preparation of substituted difluorobenzo-1,3-dioxoles 失效
标题翻译：制备取代的二氟苯-1,3-二氧杂环戊烯的方法
公开(公告)号：US5281718A
公开(公告)日：1994-01-25
申请号：US987902
申请日：1992-12-04
申请人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
发明人： Peter Ackermann , Hans-Ruedi Kanel , Bruno Schaub
IPC分类号： C07D317/46 , C07D405/04 , C07F1/00 , C07F1/02 , C07F3/00 , C07F5/02 , C07F7/08 , C07F7/10 , C07F19/00 , C07D207/36
CPC分类号： C07D405/04 , C07D317/46 , C07F1/00 , C07F1/02 , C07F19/00 , C07F3/00 , C07F5/025 , C07F7/0814 , C07F7/10 , Y02P20/55
摘要： The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkyl, nitro or by cyano, or is C.sub.1 -C.sub.12 acyl, or wherein R.sup. 1 is a radical of formula II ##STR2## wherein R.sup.5 is --CN, --CF.sub.3, --COOR.sup.2, --CONH.sup.2, --CO--NHR.sup.2 or --CONR.sub.2.sup.2, R.sup.3 and R.sup.4 are a direct bond or each is H, or R.sup.3 is H and R.sup.4 independently has the meanings of R.sup.5, or R.sup.3 and R.sup.4 together are --CH.sub.2 --NR.sup.6 --CH.sub.2 --, --CH.sub.2 --NR.sup.6 --CO-- or --CO--NR.sup.6 --CO-- wherein R.sup.6 is the radical of a removable protecting group, or wherein further R.sup.1 is a radical of formula III ##STR3## Insecticides or fungicides can be prepared from the compounds of formula I. 3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole can be prepared by reacting 4-metallo-2,2-difluorobenzodioxole (III) with an unsaturated nitrile and then with a sulfonylmethyl isocyanide in a one-pot process. The compounds III are novel intermediates.
摘要翻译： 2,2-二氟苯-1,3-二氧杂环戊烯与（a）碱金属或碱金属化合物反应，然后（b）其中Z 1为离去基团的化合物R1-Z1或与醛反应生成化合物其中R 1是-OH，-SH，-CHO，-CN，-COOH，-B（OH）2，-COX，X是Cl或Br，或者是 - COOR 2，-SiR 32或-B（OR 2）2，其中R 2为不含羟基的C 1 -C 12醇部分，其中R 1还为-C n H 2n NOR 2，n为1至4的整数，或直链或支链C 1 -C 12羟烷基，被未取代或被-F，-CN，C 1 -C 6烷氧基，苯基，氟苯基，C 1 -C 4烷氧基 - 苯基，C 1 -C 4烷硫基 - 苯基，C 1 -C 4烷基苯基，C 1 -C 4氟烷基 - 苯基，硝基苯基或氰基苯基取代，或其中R 1 是未被取代或被F，C 1 -C 4烷氧基，C 1 -C 4烷硫基，C 1 -C 4烷基，C 1 -C 4氟烷基，硝基或氰基取代的苯甲醇，或是C 1 -C 12酰基，或其中R 1是式II的基团（*化学结构*）（II）其中R5为 -CN，-CF 3，-COOR 2，-CONH 2，-CO-NHR 2或-CONR 22，R 3和R 4为直接键或各自为H或R 3为H，且R 4独立地具有R 5或R 3和R 4的含义是-CH 2 -NR 6 -CH 2 - ， - CH 2 -NR 6 -CO-或-CO-NR 6 -CO-，其中R 6是可除去保护基团的基团，或其中R 1是式III基团（*化学结构* ）（III）杀虫剂或杀真菌剂可以由式I化合物制备。3-（2,2-二氟苯并二氧杂环戊烯-4-基）-4-氰基吡咯可以通过4-金属-2,2-二氟苯并二氧杂环戊烯（III））与不饱和腈，然后在一锅法中与磺酰基甲基异氰化物反应。化合物III是新的中间体。

6. 发明授权

US5527917A Process for the preparation of 1,2-benzisothiazoles 失效
标题翻译： 1,2-苯并异噻唑的制备方法
公开(公告)号：US5527917A
公开(公告)日：1996-06-18
申请号：US301467
申请日：1994-09-07
申请人： Hans-Ruedi Kanel , Arthur Wegmann , Denis Neff
发明人： Hans-Ruedi Kanel , Arthur Wegmann , Denis Neff
IPC分类号： C07D275/04
CPC分类号： C07D275/04
摘要： A process for the preparation of 1,2-benzisothiazoles of formula I ##STR1## wherein X is in any one of the 4 possible positions of the benzene ring and is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkoxy, halo-C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy or C.sub.2 -C.sub.4 alkynyloxy, in which process a compound of formula II ##STR2## wherein X is as defined for formula I and R.sub.1 is hydrogen or an unsubstituted or substituted C.sub.1 -C.sub.12 hydrocarbon radical, is reacted in the presence of a catalytic amount of a strong acid.Compounds of formula I are known as pesticides, especially as nematicides.
摘要翻译：制备式I的1,2-苯并异噻唑的方法（I）其中X在苯环的4个可能位置中的任一个中，并且是氢，卤素，硝基，C 1 -C 4烷氧基，卤代-C 1 -C 2烷氧基，C 2 -C 4链烯氧基或C 2 -C 4炔氧基，其中X如式I和R 1所定义的式II化合物（II）为氢或未取代或取代的C 1 -C 12烃基，存在催化量的强酸。式I的化合物被称为农药，特别是作为杀线虫剂。

7. 发明授权

US5256815A Bisulfite adducts of 2,4-dihalobutraldehyde 失效
标题翻译： 2,4-二卤丁醛的亚硫酸氢盐加成物
公开(公告)号：US5256815A
公开(公告)日：1993-10-26
申请号：US975035
申请日：1992-11-12
申请人： Hans-Ruedi Kanel , John G. Dingwall
发明人： Hans-Ruedi Kanel , John G. Dingwall
IPC分类号： C07C43/12 , C07C303/22 , C07C309/08 , C07D307/20 , C07C317/18
CPC分类号： C07C43/12 , C07C303/22 , C07C309/08 , C07D307/20 , C07C2101/02
摘要： The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises a) reacting a tetrahydrofuran of formula ##STR2## with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, andb) then reacting the compound of formula III with an aqueous bisulfite solution to form a bisulfite adduct of formula ##STR4## in which X is halogen and Y is a cation equivalent of an alkali metal or alkaline earth metal ion, andc) then cyclising the adduct, in the presence of a base, with a thiolate of formula ##STR5## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl and Z is a cation equivalent of an alkali metal or alkaline earth metal ion, to form a cyclopropanecarbaldehyde of formula I, and to the individual Process Steps a), b) and c) and the combinations thereof a)+b) and b)+c), and to the novel intermediates of formulae III and IV.
摘要翻译：本发明涉及一种制备式（I）的环丙烷甲醛的方法，其中R 1是C 1 -C 4烷基或苄基，其包括：a）使式Ⅺ（II）的四氢呋喃与卤化剂反应形成式（III）的1,2,4-三卤丁基醚，其中X是卤素，R 2是未取代的或卤素取代的C 1 -C 10烷基，未被取代或被卤素，C 1 -C 4烷基或被C 1 -C 4烷基取代的C 3 -C 6环烷基 C 1 -C 4烷氧基或苯基或苄基，其各自是未被取代的或被卤素，C 1 -C 4烷基，C 1 -C 4烷氧基，硝基或氰基取代，和b）然后使式III化合物与亚硫酸氢盐水溶液反应，形成亚硫酸氢盐加合物其中X是卤素并且Y是碱金属或碱土金属离子的阳离子当量的式（IV）化合物，和c）然后在碱的存在下将加合物与式R 1 S的硫醇盐环化（ - ）Z（+）（V）其中R1是C1-C4烷基或苄基，Z是一个阳离子当量碱金属或碱土金属离子，以形成式I的环丙烷醛，以及单独的方法步骤a），b）和c）及其组合a）+ b）和b）+ c）的组合，以及该新颖的式III和IV的中间体。

8. 发明授权

US4968836A Process for the preparation of substituted cyclopropanecarbaldehydes 失效
标题翻译：制备取代环丙烷甲醛的方法
公开(公告)号：US4968836A
公开(公告)日：1990-11-06
申请号：US472677
申请日：1990-01-30
申请人： Hans-Ruedi Kanel , John G. Dingwall
发明人： Hans-Ruedi Kanel , John G. Dingwall
IPC分类号： C07C41/18 , C07C43/12 , C07C43/192 , C07C43/225 , C07C201/12 , C07C205/37 , C07C253/30 , C07C255/54 , C07C303/22 , C07C303/32 , C07C309/08 , C07C319/14 , C07C323/22 , C07D307/20
CPC分类号： C07C43/12 , C07C303/22 , C07D307/20 , C07C2101/02
摘要： The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, and(b) then reacting the compound of formula III with an aqueous bisulfite solution to form a bisulfite adduct of formula ##STR4## in which X is a halogen and Y is a cation equivalent of an alkali metal or alkaline earth metal ion, and(c) then cyclising the adduct, in the presence of a base, with a thiolate of formulaR.sub.1 --S.sup..crclbar. Z.sup..sym. (V) in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl and Z is a cation equivalent of an alkali metal or alkaline earth metal ion, to form a cyclopropanecarbaldehyde of formula I, and to the individual Process Steps (a), (b) and (c) and the combinations thereof (a)+(b) and (b)+(c), and to the novel intermediates of formulae III and IV.
摘要翻译：本发明涉及一种制备式（I）的环丙烷甲醛的方法，其中R 1是C 1 -C 4烷基或苄基，其包括（a）使式Ⅺ（II）的四氢呋喃与其中X是卤素未取代或被卤素，C 1 -C 4烷基或C 1 -C 4烷氧基取代的C 1 -C 10烷基，C 3 -C 6环烷基，或未被取代或被卤素取代的苯基或苄基， C 1-4烷基，C 1 -C 4烷氧基，硝基或氰基，与卤化剂反应形成式（Ⅺ）的1,2,4-三卤代丁基醚，其中X为卤素，R 2为未取代的或卤素取代的C 1 -C 10烷基， C 3 -C 6环烷基，其未被取代或被卤素C 1 -C 4烷基或C 1 -C 4烷氧基取代，或苯基或苄基，其各自未被取代或被卤素，C 1 -C 4烷基，C 1 -C 4烷氧基，硝基或氰基取代，和（b）使式III化合物与亚硫酸氢钠水溶液反应，形成亚硫酸氢盐加合物o （IV）其中X是卤素，Y是碱金属或碱土金属离子的阳离子当量，和（c）然后在碱的存在下将加合物与硫醇的硫醇盐环化式中R 1为C 1 -C 4烷基或苄基并且Z为碱金属或碱土金属离子的阳离子当量的式R1-S（ - ）Z（+）（V），形成式I的环丙烷甲醛，单独的方法步骤（a），（b）和（c）及其组合（a）+（b）和（b）+（c）以及式III和IV的新型中间体。

9. 发明授权

US5189227A 1,2,4-trihalobutyl ethers 失效
标题翻译： 1,2,4-三卤丁基醚
公开(公告)号：US5189227A
公开(公告)日：1993-02-23
申请号：US575458
申请日：1990-08-30
申请人： Hans-Ruedi Kanel , John G. Dingwall
发明人： Hans-Ruedi Kanel , John G. Dingwall
IPC分类号： C07C43/12 , C07C303/22 , C07C309/08 , C07D307/20
CPC分类号： C07C43/12 , C07C303/22 , C07C309/08 , C07D307/20 , C07C2101/02
摘要： 1,2,4-Trihalobutyl ethers of the formula ##STR1## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, which are useful as intermediates for the preparation of cyclopropanecarbaldehydes.
摘要翻译：式为“IMAGE”的1,2,4-三卤代丁基醚，其中X为卤素，R 2为未取代的或卤素取代的C 1 -C 10烷基，未被取代或被卤素，C 1 -C 4烷基或C 1 -C 4烷基取代的C 3 -C 6环烷基 -C 1-4烷氧基或苯基或苄基，其各自是未被取代的或被卤素，C 1 -C 4烷基，C 1 -C 4烷氧基，硝基或氰基取代的，其可用作制备环丙烷甲醛的中间体。

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