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Denotivir, Wratizolin, Vratizolin, T15, ITCL

氰基甲酸乙酯Chemical Name: 5-(Benzoylamino)-N-(4-chlorophenyl)-3-methyl-4-isothiazolecarboxamide; 5-Benzamido-4'-chloro-3-methyl-4-isothiazolecarboxanilide
CAS No. 51287-57-1
项目整合开发状态: Phase I
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Two different routes have been described for the preparation of title compound:1) 3-Methyl-5-aminoisothiazole-4-carboxylic acid (I) is reacted with benzoyl chloride in acetone solution and in the presence of pyridine to yield the benzamide (II),which by reaction with SOCl2 is converted to the lactam (III).The reaction of lactam (III) with p-chloroaniline in anhydrous ethanol gives the p-chlorophenylamide (vratizolin).2) The reaction of 3-methyl-5-benzoylamino-4-isothiazolecarboxylic acid (II) with chloroformic ethyl ester gives the mixed anhydride,which,when heated with p-chloroanitine in anhydrous ethanol forms title compound.Vratizolin is also a product of the reaction of the acid (II) with p-chloroaniline in the presence of dicyclohexylcarbodiimide.
📌 参考资料/链接:
参考文献标题:Vratizolin
文献作者:Machon,Z.
参考来源:Drugs Fut 1988,13(5),426

📄 详细内容


合成路线:Two different routes have been described for the preparation of title compound:1) 3-Methyl-5-aminoisothiazole-4-carboxylic acid (I) is reacted with benzoyl chloride in acetone solution and in the presence of pyridine to yield the benzamide (II),which by reaction with SOCl2 is converted to the lactam (III).The reaction of lactam (III) with p-chloroaniline in anhydrous ethanol gives the p-chlorophenylamide (vratizolin).2) The reaction of 3-methyl-5-benzoylamino-4-isothiazolecarboxylic acid (II) with chloroformic ethyl ester gives the mixed anhydride,which,when heated with p-chloroanitine in anhydrous ethanol forms title compound.Vratizolin is also a product of the reaction of the acid (II) with p-chloroaniline in the presence of dicyclohexylcarbodiimide.

参考文献标题:Synthesis and properties of 3-methyl-5-benzoylaminoiothiazole-4-carboxilic acid derivatives
文献作者:Machon,Z.
参考来源:Diss Pharm Pharmacol 1969,21(4),325


合成路线:Two different routes have been described for the preparation of title compound:1) 3-Methyl-5-aminoisothiazole-4-carboxylic acid (I) is reacted with benzoyl chloride in acetone solution and in the presence of pyridine to yield the benzamide (II),which by reaction with SOCl2 is converted to the lactam (III).The reaction of lactam (III) with p-chloroaniline in anhydrous ethanol gives the p-chlorophenylamide (vratizolin).2) The reaction of 3-methyl-5-benzoylamino-4-isothiazolecarboxylic acid (II) with chloroformic ethyl ester gives the mixed anhydride,which,when heated with p-chloroanitine in anhydrous ethanol forms title compound.Vratizolin is also a product of the reaction of the acid (II) with p-chloroaniline in the presence of dicyclohexylcarbodiimide.

参考文献标题:p-Chlorophenylamide of 3-methyl-5-benzoyl-aminoiso
文献作者:Machon,Z.
参考来源:Arch Immunol Ther Exp 1983,31579


合成路线:Two different routes have been described for the preparation of title compound:1) 3-Methyl-5-aminoisothiazole-4-carboxylic acid (I) is reacted with benzoyl chloride in acetone solution and in the presence of pyridine to yield the benzamide (II),which by reaction with SOCl2 is converted to the lactam (III).The reaction of lactam (III) with p-chloroaniline in anhydrous ethanol gives the p-chlorophenylamide (vratizolin).2) The reaction of 3-methyl-5-benzoylamino-4-isothiazolecarboxylic acid (II) with chloroformic ethyl ester gives the mixed anhydride,which,when heated with p-chloroanitine in anhydrous ethanol forms title compound.Vratizolin is also a product of the reaction of the acid (II) with p-chloroaniline in the presence of dicyclohexylcarbodiimide.

参考文献标题:New isothiazole derivatives.I.Relations between chemical structure and biological activities
文献作者:Machon,Z.; et al.
参考来源:Arch Immunol Ther Exp 1973,21(6),883-889


合成路线:Two different routes have been described for the preparation of title compound:1) 3-Methyl-5-aminoisothiazole-4-carboxylic acid (I) is reacted with benzoyl chloride in acetone solution and in the presence of pyridine to yield the benzamide (II),which by reaction with SOCl2 is converted to the lactam (III).The reaction of lactam (III) with p-chloroaniline in anhydrous ethanol gives the p-chlorophenylamide (vratizolin).2) The reaction of 3-methyl-5-benzoylamino-4-isothiazolecarboxylic acid (II) with chloroformic ethyl ester gives the mixed anhydride,which,when heated with p-chloroanitine in anhydrous ethanol forms title compound.Vratizolin is also a product of the reaction of the acid (II) with p-chloroaniline in the presence of dicyclohexylcarbodiimide.
参考文献标题:ITCI
文献作者:Kolwas,J.
参考来源:Drugs Fut 1981,6(8),475


产品链接: CAS No. 51287-57-1››