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1. 发明授权

US4315094A Preparation of 4-amino-6-tert.-butyl-3-alkylthio-1,2,4-triazin-5(4H)-one 失效
标题翻译： 4-氨基-6-叔丁基-3-烷硫基-1,2,4-三嗪-5（4H） - 酮的制备
公开(公告)号：US4315094A
公开(公告)日：1982-02-09
申请号：US235495
申请日：1981-02-19
申请人： Gerhard Bonse , Heinz U. Blank , Hans Kratzer
发明人： Gerhard Bonse , Heinz U. Blank , Hans Kratzer
IPC分类号： C07D253/06 , C07C51/06 , C07D253/075
CPC分类号： C07D253/075 , C07C51/06
摘要： In the preparation of 4-amino-6-tert.-butyl-3-alkylthio-1,2,4-triazin-5-(4H)-one of the formula ##STR1## wherein (1) pivaloyl cyanide of the formula(CH.sub.3).sub.3 C--CO--CNis reacted to form a derivative of pyruvic acid, (2) the pyruvic acid derivative is condensed with thiocarbohydrazide of the formulaNH.sub.2 --NH--CS--NH--NH.sub.2to form 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one of the formula ##STR2## and (3) this is alkylated, the improvement which comprises effecting step (1) by reaction with a carboxylic acid anhydride of the formulaR--CO--O--CO--Rin which R is an optionally substituted aliphatic radical with up to 8 carbon atoms or an optionally substituted phenyl radical, in the presence of a strong acid at a temperature between about -50.degree. and +150.degree. C., and then adding water to the reaction mixture, thereby to form trimethylpyruvic acid N-acylamide of the formula(CH.sub.3).sub.3 C--CO--CO--NH--CO--R.
摘要翻译：在制备式（IMAGE）的4-氨基-6-叔丁基-3-烷硫基-1,2,4-三嗪-5-（4H） - 酮中，其中（1）式（1）的新戊酰氰 CH3）3C-CO-CN反应形成丙酮酸的衍生物，（2）丙酮酸衍生物与式NH2-NH-CS-NH-NH2的硫代酰肼缩合形成4-氨基-6-叔丁基。丁基-3-巯基-1,2,4-三嗪-5（4H） - 酮，和（3）将其烷基化，其改进包括通过与羧酸反应进行步骤（1）式R-CO-O-CO-R的酸酐，其中R是具有至多8个碳原子的任选取代的脂族基团或任选取代的苯基基团，在强酸存在下，在约-50℃ 和+ 150℃，然后向反应混合物中加入水，从而形成式（CH 3）3 C-CO-CO-NH-CO-R的三甲基丙酮酸N-酰基酰胺。

2. 发明授权

US4328340A Preparation of 4-amino-6-tert.-butyl-3-alkylthio-1,2,4-triazin-5-(4H)-ones 失效
标题翻译：制备4-氨基-6-叔丁基-3-烷硫基-1,2,4-三嗪-5-（4H） - 酮
公开(公告)号：US4328340A
公开(公告)日：1982-05-04
申请号：US235496
申请日：1981-02-19
申请人： Gerhard Bonse , Heinz U. Blank , Hans Kratzer
发明人： Gerhard Bonse , Heinz U. Blank , Hans Kratzer
IPC分类号： C07D253/06 , C07D253/075
CPC分类号： C07D253/075
摘要： In the preparation of 4-amino-6-tert.-butyl-3-methylthio-1,2,4-triazin-5-(4H)-one of the formula ##STR1## wherein pivaloyl cyanide of the formula(CH.sub.3).sub.3 C--CO--CNis reacted to form an intermediate, the intermediate is condensed with thiocarbohydrazide of the formulaNH.sub.2 --NH--CS--NH--NH.sub.2to form 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5-(4H)-one of the formula ##STR2## and the 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5-(4H)-one is alkylated to replace the H atom on the sulphur by --C.sub.1-4 --alkyl, the improvement which comprises reacting the pivaloyl cyanide with a carboxylic acid anhydride of the formulaR--CO--O--CO--Rin which R is an optionally substituted aliphatic radical with up to 8 carbon atoms or an optionally substituted phenyl radical, in the presence of a strong acid at a temperature between about -50.degree. and +150.degree. C., and then directly reacting the reaction mixture thus obtained with the thiocarbahydrazide. Advantageously R is CH.sub.3, the strong acid is concentrated sulphuric acid, the pivaloyl cyanide is effected at a temperature between about 0.degree. and 100.degree. C., the condensation with thiocarbohydrazide is effected, in the presence of a mineral acid, in an aqueous or aqueous-alcoholic medium, and the alkylation is effected using methyl iodide or methyl bromide in the presence of sodium hydroxide at about 0.degree. to 50.degree. C.
摘要翻译：在制备式（CH 3）3 C的新戊酰基氰的4-氨基-6-叔丁基-3-甲硫基-1,2,4-三嗪-5-（4H） - 酮中， -CO-CN反应形成中间体，中间体与式NH 2 -NH-CS-NH-NH 2的硫代碳酰肼缩合形成4-氨基-6-叔丁基-3-巯基-1,2，（4H） - 酮和4-氨基-6-叔丁基-3-巯基-1,2,4-三嗪-5-（4H） - 酮是烷基化以用-C 1-4烷基取代硫上的H原子，其改进包括使新戊酰氰与式R-CO-O-CO-R的羧酸酐反应，其中R是任选取代的脂族具有多达8个碳原子的基团或任选取代的苯基，在强酸存在下，在约-50至+ 150℃之间的温度下，然后将由此获得的反应混合物与硫代碳酰肼直接反应。有利地，R是CH 3，强酸是浓硫酸，新戊酰氰在约0℃至100℃的温度下进行，与硫代碳酰肼的缩合在无机酸的存在下，在水或水性醇介质，在氢氧化钠存在下，在约0〜50℃下，使用甲基碘或甲基溴进行烷基化。

3. 发明授权

US4309538A Preparation of 4-amino-6-tert.-butyl-3-alkylthio-1,2,4-triazin-5(4H)-ones 失效
标题翻译：制备4-氨基-6-叔丁基-3-烷硫基-1,2,4-三嗪-5（4H） - 酮
公开(公告)号：US4309538A
公开(公告)日：1982-01-05
申请号：US227442
申请日：1981-01-22
申请人： Thomas Schmidt , Andreas Wittig , Hans-Peter Sehnem , Hans Kratzer , Rolf-Jurgen Singer
发明人： Thomas Schmidt , Andreas Wittig , Hans-Peter Sehnem , Hans Kratzer , Rolf-Jurgen Singer
IPC分类号： C07D253/07 , C07D253/075 , C07D253/06
CPC分类号： C07D253/075 , C07D253/07
摘要： In the preparation of 4-amino-6-tert.-butyl-3-alkylthio-1,2,4-triazin-5(4H)-ones of the formula ##STR1## wherein (a) pivaloyl cyanide of the formula(CH.sub.3).sub.3 C--CO--CNis converted to a derivative of trimethylpyruvic acid, (b) the derivative is condensed with thiocarbohydrazide of the formulaH.sub.2 N--NH--CS--NH--NH.sub.2to form 4-amino-6-tert.-butyl-3-mercapto-1,2,4-triazin-5(4H)-one, and (c) that is alkylated to form the indicated end products, the improvement which comprises effecting (a) by reacting the pivaloyl cyanide with a strong anhydrous inorganic acid at about -50.degree. to +50.degree. C. thereby to form trimethylpyruvic acid amide. The derivative in (a) can be trimethylpyruvic acid amide or it may first be saponified to the free acid. The inorganic acid in (a) can be hydrochloric or hydrobromic acid in glacial acetic acid, or it can be concentrated sulphuric acid plus some chloride ion and followed by water. Trimethyl pyruvic acid amide is a new compound.
摘要翻译：在制备式（IMA）的4-氨基-6-叔丁基-3-烷硫基-1,2,4-三嗪-5（4H） - 酮的方法中，其中（a）式（CH3）的新戊酰氰）将3C-CO-CN转化为三甲基丙酮酸的衍生物，（b）将该衍生物与式H2N-NH-CS-NH-NH 2的硫代碳酰肼缩合形成4-氨基-6-叔丁基-3 - 巯基-1,2,4-三嗪-5（4H） - 酮，和（c）烷基化形成指定的最终产物，其改进包括通过使新戊酰氰与强无机无机无机酸在约-50℃至+ 50℃，从而形成三甲基丙酮酸酰胺。（a）中的衍生物可以是三甲基丙酮酸酰胺，或者它可以首先被皂化成游离酸。（a）中的无机酸可以是冰醋酸中的盐酸或氢溴酸，也可以是浓硫酸加一些氯离子，然后是水。三甲基丙酮酸酰胺是一种新的化合物。

4. 发明授权

US4564704A Production of 3,3-dimethyl-2-oxo-butyric acid salt 失效
标题翻译：制备3,3-二甲基-2-氧代 - 丁酸盐
公开(公告)号：US4564704A
公开(公告)日：1986-01-14
申请号：US227552
申请日：1981-01-22
申请人： Karlfried Dickore , Hans D. Engels , Hans Kratzer , Walter Merz
发明人： Karlfried Dickore , Hans D. Engels , Hans Kratzer , Walter Merz
IPC分类号： C07C45/63 , C07C51/00 , C07C59/185 , C07C51/285 , C07C51/373
CPC分类号： C07C59/185 , C07C45/63 , C07C51/00
摘要： Dichloropinacolone is produced by introducing into pinacolone twice the molar amount of chlorine, the exothermic reaction mass being cooled initially to maintain the temperature below about 50.degree. C. until about 60 to 80% of the chlorine has been introduced, and then heating the reaction mass to a temperature above 50.degree. C. during introducing of the remainder of the chlorine, thereby to produce dichloropinacolone, and terminating chlorine introduction when the dichloropinacolone content of the reaction mass is at least about 97%. The molten product is added to an aqueous solution of an alkali maintained at a temperature of at least about 50.degree. C., the alkali being present in more than three times the molar amount of the dichloropinacolone. To the resulting solution of a salt of 3,3-dimethyl-2-hydroxy-butyric acid, brought to a pH of about 9 to 12, there is added approximately the stoichiometric amount of potassium permanganate. Solid MnO.sub.2 precipitates out and is separated from the substantially pure dissolved salt of 3,3-dimethyl-2-oxo-butyric acid. The product is a known compound suited for further syntheses.
摘要翻译：通过将频倍他康酮引入两倍于氯的摩尔量来产生二氯可乐乐，最初冷却放热反应物质以保持温度低于约50℃，直到引入约60至80％的氯，然后加热反应物质在导入剩余的氯的过程中温度高于50℃，从而产生二氯靛那烯，并且当反应物质的二氯新戊酮酮含量为至少约97％时终止氯引入。将熔融产物加入到保持在至少约50℃温度的碱的水溶液中，碱的存在量是氯苯腈的摩尔量的三倍以上。向所得到的3,3-二甲基-2-羟基 - 丁酸的盐溶液中加入大约9-12的pH，加入大约化学计量的高锰酸钾。固体MnO 2析出并与3,3-二甲基-2-氧代 - 丁酸的基本上纯的溶解盐分离。该产物是适用于进一步合成的已知化合物。

5. 发明授权

US4052460A Production of 3,3-dimethyl-2-oxo-butyric acid salt 失效
标题翻译：制备3,3-二甲基-2-氧代 - 丁酸盐
公开(公告)号：US4052460A
公开(公告)日：1977-10-04
申请号：US650651
申请日：1976-01-20
申请人： Karlfried Dickore , Hans Dieter Engels , Hans Kratzer , Walter Merz
发明人： Karlfried Dickore , Hans Dieter Engels , Hans Kratzer , Walter Merz
IPC分类号： C07C49/16 , C07C45/00 , C07C45/63 , C07C51/00 , C07C51/373 , C07C59/01 , C07C59/185 , C07C67/00
CPC分类号： C07C59/185 , C07C45/63 , C07C51/00
摘要： Dichloropinacolone is produced by introducing into pinacolone twice the molar amount of chlorine, the exothermic reaction mass being cooled initially to maintain the temperature below about 50.degree. C until about 60 to 80% of the chlorine has been introduced, and then heating the reaction mass to a temperature above 50.degree. C during introducing of the remainder of the chlorine, thereby to produce dichloropinacolone, and terminating chlorine introduction when the dichloropinacolone content of the reaction mass is at least about 97%. The molten product is added to an aqueous solution of an alkali maintained at a temperature of at least about 50.degree. C, the alkali being present in more than three times the molar amount of the dichloropinacolone. To the resulting solution of a salt of 3,3-dimethyl-2-hydroxy-butyric acid, brought to a pH of about 9 to 12, there is added approximately the stoichiometric amount of potassium permanganate. Solid MnO.sub.2 precipitates out and is separated from the substantially pure dissolved salt of 3,3-dimethyl-2-oxo-butyric acid. The product is a known compound suited for further syntheses.

6. 发明授权

US4898974A Production of 3,3-dimethyl-2-oxo-butyric acid salt 失效
标题翻译：制备3,3-二甲基-2-氧代 - 丁酸盐
公开(公告)号：US4898974A
公开(公告)日：1990-02-06
申请号：US726218
申请日：1985-04-23
申请人： Karlfried Dickore , Hans D. Engels , Hans Kratzer , Walter Merz
发明人： Karlfried Dickore , Hans D. Engels , Hans Kratzer , Walter Merz
IPC分类号： C07C45/63 , C07C51/00 , C07C59/185
CPC分类号： C07C59/185 , C07C45/63 , C07C51/00
摘要： Dichloropinacolone is produced by introducing into pinacolone twice the molar amount of chlorine, the exothermic reaction mass being cooled initially to maintain the temperature below about 50.degree. C. until about 60 to 80% of the chlorine has been introduced, and then heating the reaction mass to a temperature above 50.degree. C. during introducing of the remainder of the chlorine, thereby to produce dichloropinacolone, and terminating chlorine introduction when the dichloropinacolone content of the reaction mass is at least about 97%. The molten product is added to an aqueous solution of an alkali maintained at a temperature of at least about 50.degree. C., the alkali being present in more than three times the molar amount of the dichloropinacolone. To the resulting solution of a salt of 3,3-dimethyl-2-hydroxy-butyric acid, brought to a pH of about 9 to 12, there is added approximately the stoichiometric amount of potassium permanganate. Solid MnO.sub.2 precipitates out and is separated from the substantially pure dissolved salt of 3,3-dimethyl-2-oxo-butyric acid. The produce is a known compound suited for further syntheses.
摘要翻译：通过将频倍他康酮引入两倍于氯的摩尔量来产生二氯可乐乐，最初冷却放热反应物质以保持温度低于约50℃，直到引入约60至80％的氯，然后加热反应物质在导入剩余的氯的过程中温度高于50℃，从而产生二氯一可乐酮，并且当反应物质的二氯新戊酮酮含量为至少约97％时终止氯引入。将熔融产物加入到保持在至少约50℃温度的碱的水溶液中，碱的存在量是氯苯腈的摩尔量的三倍以上。向所得到的3,3-二甲基-2-羟基 - 丁酸的盐溶液中加入大约9-12的pH，加入大约化学计量的高锰酸钾。固体MnO 2析出并与3,3-二甲基-2-氧代 - 丁酸的基本上纯的溶解盐分离。该产物是适用于进一步合成的已知化合物。

7. 发明授权

US4360479A Process for the preparation of acyl cyanide compounds 失效
标题翻译：酰基氰化合物的制备方法
公开(公告)号：US4360479A
公开(公告)日：1982-11-23
申请号：US276774
申请日：1981-06-24
申请人： Kurt Findeisen , Hans Kratzer , Manfred Lenthe
发明人： Kurt Findeisen , Hans Kratzer , Manfred Lenthe
IPC分类号： C07C255/17 , C07C51/08 , C07C67/00 , C07C253/00 , C07C255/40 , C07C255/56 , C07D253/06 , C07D253/07 , C07C51/083
CPC分类号： C07D253/07 , C07C255/00
摘要： This invention relates to a new process for the preparation of acyl cyanides of the general formulaR.sup.1 --CO--CN (I)wherein R.sup.1 is an optionally substituted alkyl radical up to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring, which process comprises reacting a carboxylic acid anhydride of the formulaR.sup.1 --CO--O--CO--R.sup.1 (II)with an alpha-hydroxynitrile of the formula ##STR1## in which R.sup.2 and R.sup.3 are identical or different and represent a hydrogen atom, an optionally substituted alkyl radical with 1 to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring. The acyl cyanides (I) are known compounds and can be used as starting material for the synthesis of herbicides.
摘要翻译：本发明涉及用于制备通式为R 1 -CO-CN（I）的酰基氰的新方法，其中R 1为任选取代的至多18个碳原子的烷基，具有3至12个碳原子的任选取代的环烷基，任选取代的芳基或任选取代的5-或6-元杂环基，其还可以与苯环稠合，该方法包括使式R 1 -CO-O-CO-R 1的羧酸酐（II）与式（III）的α-羟基腈，其中R 2和R 3相同或不同并且表示氢原子，任选取代的具有1至18个碳原子的烷基，任选取代的环烷基与 3至12个碳原子，任选取代的芳基或任选取代的5或6元杂环基，其还可以与苯环稠合。酰基氰化物（I）是已知的化合物，可用作合成除草剂的原料。

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