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1. 发明授权

US4009161A 6-Methyl-2H-1,3-oxazin-2,4(3H)dione-3-sulfohalides 失效
标题翻译： 6-甲基-2H-1,3-恶嗪-2,4（3H）二酮-3-磺酰卤
公开(公告)号：US4009161A
公开(公告)日：1977-02-22
申请号：US596227
申请日：1975-07-16
申请人： Hartmut Pietsch , Karl Clauss , Erwin Schmidt , Harald Jensen
发明人： Hartmut Pietsch , Karl Clauss , Erwin Schmidt , Harald Jensen
IPC分类号： C07D265/06 , C07D265/10 , C07D273/00 , C07D295/00
CPC分类号： C07D265/06
摘要： 3-Sulfohalides of 6-methyl-2H-1,3-oxazin-2,4(3H)-dione of the formula I ##STR1## in which X represents fluorine or chlorine are prepared by reacting fluorosulfonyl isocyanate or chlorosulfonyl isocyanate, at a temperature of from -35.degree. to +70.degree. C, optionally in the presence of an inert solvent, with diketene, acetoacetyl fluoride, acetoacetyl chloride, acetoacetic acid or an isopropenyl ester of the formula CH.sub.2 =C(OOCR)-CH.sub.3 in which R represents an alkyl radical having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl or benzyl radical.
摘要翻译：通过使氟代磺酰基异氰酸酯或氯磺酰基异氰酸酯反应制备式I的6-甲基-2H-1,3-恶嗪-2,4（3H） - 二酮的3-磺酰卤，其中X代表氟或氯，，在-35至+70℃的温度下，任选在惰性溶剂存在下，与二烯酮，乙酰乙酰氟，乙酰乙酰氯，乙酰乙酸或式CH2 = C（OOCR）-CH3的异丙烯基酯其中R表示具有1至4个碳原子的烷基，取代或未取代的苯基或苄基。

2. 发明授权

US4052453A Process for preparing acetoacetamide-N-sulfofluoride 失效
标题翻译：制备ACETOACETAMIDE-N-SULFOFLUORIDE的方法
公开(公告)号：US4052453A
公开(公告)日：1977-10-04
申请号：US618405
申请日：1975-10-01
申请人： Hartmut Pietsch , Karl Clauss , Harald Jensen , Erwin Schmidt
发明人： Hartmut Pietsch , Karl Clauss , Harald Jensen , Erwin Schmidt
IPC分类号： C07C307/00 , C07C20060101 , C07C67/00 , C07C301/00 , C07C303/36 , C07D291/06 , C07C143/70 , C07C143/72
CPC分类号： C07C307/00
摘要： Process for preparing acetoacetamide-N-sulfofluoride by reacting amidosulfofluoride at a temperature of from 50.degree. to 100.degree. C with diketene, optionally in the presence of inert solvents or diluents.

3. 发明授权

US3993689A .beta.-Acyloxy-crotonic acid amide-N-sulfohalides and a process for their preparation 失效
标题翻译： {62-氰基 - 巴豆酸酰胺-N-磺酰卤化物及其制备方法
公开(公告)号：US3993689A
公开(公告)日：1976-11-23
申请号：US596218
申请日：1975-07-16
申请人： Erwin Schmidt , Karl Clauss , Hartmut Pietsch , Harald Jensen
发明人： Erwin Schmidt , Karl Clauss , Hartmut Pietsch , Harald Jensen
IPC分类号： C07C307/00 , C07C67/00 , C07C301/00 , C07C303/00 , C07D205/08 , C07D291/06 , C07C161/00
CPC分类号： C07D205/08 , C07D291/06
摘要： Compounds of the formula ##SPC1##In which R represents an alkyl radical having from 1 to 4 carbon atoms and Hal stands for fluorine or chlorine are prepared by reacting at a temperature of from -40.degree. to +20.degree. C an i-propenylalkanoic acid ester of the formula ##EQU1## with an isocyanate of the formulaO=C=N--SO.sub.2 Hal (V)in which R and Hal have the same meaning as above, and isolating the compound of formula III.
摘要翻译：式+ q，10 IN的化合物，其中R表示具有1至4个碳原子的烷基，Hal表示氟或氯，通过在-40℃至+ 20℃的温度下反应制备异丙烯基链烷酸其中R和Hal具有与上述相同的含义，分子式为CH 2 RC（O）-OC = CH 2（Ⅳ）的异氰酸酯与式O = C = N-SO 2 Hal 的式III。

4. 发明授权

US3969347A Process for the manufacture of the potassium salt of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide 失效
标题翻译：制备6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物的钾盐的方法
公开(公告)号：US3969347A
公开(公告)日：1976-07-13
申请号：US596217
申请日：1975-07-16
申请人： Erwin Schmidt , Karl Clauss , Hartmut Pietsch , Harald Jensen
发明人： Erwin Schmidt , Karl Clauss , Hartmut Pietsch , Harald Jensen
IPC分类号： A23L27/30 , C07D291/06 , C07D291/08
CPC分类号： C07D291/06 , A23L27/30
摘要： The potassium salt practically free of fluoride of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide is prepared by cyclization of acetoacetamide-N-sulfofluoride with at least two moles potassium hydroxide, potassium methylate or a mixture of potassium hydroxide and potassium methylate per mole of sulfofluoride in methanol as solvent containing less than 50 % by weight of water at a temperature of from -20.degree. to +60.degree.C and separating the crystalline potassium salt of the oxathiazinone dioxide from the reaction solution. The compound obtained has a pure sweet taste.
摘要翻译：实际上不含6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物的氟化物的钾盐通过使至少两摩尔的乙酰乙酰胺-N-氟磺酸盐环化来制备氢氧化钾，甲醇钾或氢氧化钾和甲醇钾的混合物，相对于甲醇中的每摩尔磺氟化物，在-20℃至+ 60℃的温度下含有少于50重量％的水，并分离结晶钾盐的氧化二嗪二氧化物。所得化合物具有纯甜味。

5. 发明授权

US3968106A Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and its use as sweetener 失效
标题翻译：制备6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物的方法及其作为甜味剂的用途
公开(公告)号：US3968106A
公开(公告)日：1976-07-06
申请号：US596226
申请日：1975-07-16
申请人： Karl Clauss , Hartmut Pietsch , Erwin Schmidt , Harald Jensen
发明人： Karl Clauss , Hartmut Pietsch , Erwin Schmidt , Harald Jensen
IPC分类号： A23L27/30 , C07D291/06 , C07D291/08
CPC分类号： C07D291/06 , A23L27/30
摘要： 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and the nontoxic salts thereof are prepared by reacting acetone and fluorosulfonyl isocyanate in a molar proportion of from 14:1 to 150:1 at a temperature of from 0.degree. to 60.degree.C, distilling off the excess acetone from the reaction mixture with acetoacetamide-N-sulfofluoride and bringing about cyclization by a treatment with bases at a pH of from 5 to 12. The oxathiazinone derivatives are used as sweeteners.
摘要翻译： 6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物及其无毒盐通过使丙酮和氟磺酰基异氰酸酯以14:1的摩尔比例反应制备成 150:1，在0℃至60℃的温度下，用乙酰乙酰胺-N-氟化铵从反应混合物中蒸馏出过量的丙酮，通过碱处理使其在5至12的pH下进行环化。恶噻嗪酮衍生物用作甜味剂。

6. 发明授权

US3969348A Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide 失效
标题翻译：制备6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物的方法
公开(公告)号：US3969348A
公开(公告)日：1976-07-13
申请号：US596231
申请日：1975-07-16
申请人： Hartmut Pietsch , Karl Clauss , Erwin Schmidt , Harald Jensen
发明人： Hartmut Pietsch , Karl Clauss , Erwin Schmidt , Harald Jensen
IPC分类号： C07D265/06 , C07D291/06
CPC分类号： C07D265/06
摘要： 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide or the nontoxic salts thereof is prepared by reacting 6-methyl-2,3-dihydro-1,3-oxazin-2,4-dione-3-sulfo-fluoride of the formula ##EQU1## with at least 1 mole water per mole of fluoride to obtain acetoacetamide-N-sulfo-fluoride with splitting off of CO.sub.2, treating the acetoacetamide-N-sulfofluoride with an aqueous and/or alcoholic base and isolating the oxathiazinone or the salts thereof.
摘要翻译： 6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物或其无毒盐通过6-甲基-2,3-二氢-1,3- 具有至少1摩尔水/摩尔氟化物的式CH3 | HC = C || O = CO ||N-CO | SO2F的2,3-恶嗪-2,4-二酮-3-磺酰氟，得到乙酰乙酰胺-N-磺基氟化物，分解出二氧化碳，用水和/或酒精碱处理乙酰乙酰胺-N-磺氟化物，并分离出恶噻嗪酮或其盐。

7. 发明授权

US3968107A Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide 失效
标题翻译：制备6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物的方法
公开(公告)号：US3968107A
公开(公告)日：1976-07-06
申请号：US596247
申请日：1975-07-16
申请人： Karl Clauss , Erwin Schmidt , Hartmut Pietsch , Harald Jensen
发明人： Karl Clauss , Erwin Schmidt , Hartmut Pietsch , Harald Jensen
IPC分类号： A23L27/30 , C07D291/06
CPC分类号： C07D291/06
摘要： 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and the nontoxic salts thereof are prepared by reacting acetoacetic acid with fluorosulfonyl isocyanate at a temperature of from -20.degree.C to +50.degree.C in the presence of from 0.5 to 2 moles, calculated on the FSI used, of an alkali methal fluoride or a tertiary amine of the formulaN(R.sub.1)(R.sub.2)(R.sub.3)in which R.sub.1, R.sub.2, R.sub.3 represent identical or different alkyl radicals having from 1 to 10 carbon atoms, two of the radicals R.sub.1 to R.sub.3 optionally form together an alkylene radical having from 4 to 5 carbon atoms which may contain N, O, or S as hetero atom, or one of the radicals R.sub.1 to R.sub.3 represents a phenyl radical, or of pyridine or quinoline, or of a mixture of the aforesaid compounds, and transforming the salt of acetoacetamide-N-sulfofluoride obtained into the oxathiazinone salt or the free oxathiazinone by a treatment with aqueous and/or alcoholic bases.
摘要翻译： 6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮-2,2-二氧化物及其无毒盐通过乙酰乙酸与氟磺酰基异氰酸酯在-20℃的温度下反应制备在式（I）（R 2）（R 3）的碱金属氟化物或叔胺的存在下，在0.5〜2摩尔的存在下，在0.5〜2摩尔的存在下，将R 1，R 2，R 3 代表具有1至10个碳原子的相同或不同的烷基，基团R 1至R 3中的两个任选地可以含有具有4至5个碳原子的亚烷基，其可以含有N，O或S作为杂原子，或者基团R 1至R 3表示苯基或吡啶或喹啉或上述化合物的混合物，并将获得的乙酰乙酰胺-N-磺酰氟盐转化为氧杂二恶嗪酮盐或游离的恶唑二酮通过用水和 /或酒精基地。

8. 发明授权

US4625024A Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts 失效
标题翻译：制备6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮2,2-二氧化物及其无毒盐的方法
公开(公告)号：US4625024A
公开(公告)日：1986-11-25
申请号：US762563
申请日：1985-08-05
申请人： Erwin Schmidt , Karl Clauss
发明人： Erwin Schmidt , Karl Clauss
IPC分类号： A23L27/30 , C07D291/06
CPC分类号： C07D291/06
摘要： 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts are prepared by reacting acetoacetamide with an S-O compound of the formula IFSO.sub.2 Y (I)wherein Y.dbd.F, Cl, --OSO.sub.2 F or --OSO.sub.2 Cl, preferably only F,in the presence of bases.The non-toxic salts--especially the potassium salt--are valuable synthetic sweeteners.
摘要翻译： 6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮2,2-二氧化物及其无毒盐通过使乙酰乙酰胺与式I FSO 2 Y（I）的SO化合物反应制备，其中在碱的存在下，Y = F，Cl，-OSO 2 F或-OSO 2 Cl，优选仅F。无毒盐 - 特别是钾盐 - 是有价值的合成甜味剂。

9. 发明授权

US4607100A Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts 失效
标题翻译：制备6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮2,2-二氧化物及其无毒盐的方法
公开(公告)号：US4607100A
公开(公告)日：1986-08-19
申请号：US714177
申请日：1985-03-20
申请人： Karl Clauss , Adolf Linkies , Dieter Reuschling
发明人： Karl Clauss , Adolf Linkies , Dieter Reuschling
IPC分类号： A23L27/30 , B01J31/00 , B01J31/02 , B01J31/24 , C07B61/00 , C07C303/34 , C07C307/02 , C07C311/46 , C07D291/06
CPC分类号： C07D291/06
摘要： 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by(a) reacting, in an inert organic solvent, a salt of sulfamic acid, which is at least partially soluble therein, with at least approximately the equimolar amount of an acetoacetylating agent, in the presence of an amine or phosphine catalyst, and by cyclizing the acetoacetamide-N-sulfonate which is formed in this reaction, or the free sulfonic acid,(b) by the action of at least approximately the equimolar amount of SO.sub.3, where appropriate in an inert inorganic or organic solvent, to give 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide, which is produced in the form of the acid in this reaction;it is possible, if desired, to obtain from the acid form(c) the appropriate salts by neutralization with bases.The non-toxic salts--in particular the potassium salt--are valuable synthetic sweeteners.
摘要翻译： 6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮2,2-二氧化物通过以下步骤制备：（a）在惰性有机溶剂中使氨基磺酸盐至少至少约等摩尔量的乙酰乙酰化剂，在胺或膦催化剂的存在下，通过使在该反应中形成的乙酰乙酰胺-N-磺酸盐或游离磺酸（b ）通过至少近似等摩尔量的SO 3的作用，在适当的惰性无机或有机溶剂中，得到6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮2,2 在该反应中以酸的形式产生的二氧化物; 如果需要，可以通过用碱中和从酸形式（c）获得适当的盐。无毒盐 - 特别是钾盐 - 是有价值的合成甜味剂。

10. 发明授权

US4638063A Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts 失效
标题翻译：制备6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮2,2-二氧化物及其无毒盐的方法
公开(公告)号：US4638063A
公开(公告)日：1987-01-20
申请号：US799622
申请日：1985-11-19
申请人： Karl Clauss , Adolf Linkies , Dieter Reuschling
发明人： Karl Clauss , Adolf Linkies , Dieter Reuschling
IPC分类号： A23L27/30 , C07D291/06
CPC分类号： C07D291/06
摘要： 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by reaction of acetoacetamide with at least approximately twice the molar amount of SO.sub.3 per mole of acetoacetamide, if appropriate in an inert inorganic or organic solvent. Relevant salts can be obtained, using bases, from the product which results in the form of the acid.The non-toxic salts, in particular the potassium salt, are valuable synthetic sweeteners.
摘要翻译： 6-甲基-3,4-二氢-1,2,3-氧杂噻嗪-4-酮2,2-二氧化物是通过乙酰乙酰胺与摩尔量的SO 3 /摩尔乙酰乙酰胺反应而制备的，如果合适的话惰性无机或有机溶剂。使用碱可以从产生酸形式的产物获得相关的盐。无毒盐，特别是钾盐是有价值的合成甜味剂。

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