2-bromo-N-(2,6-dimethylphenyl)propanamide -Drug Synthesis Database

【结构式】

【分子编号】33594

【品名】2-bromo-N-(2,6-dimethylphenyl)propanamide

【CA登记号】

【分子式】C₁₁H₁₄BrNO

【分子量】256.1423

【元素组成】C 51.58% H 5.51% Br 31.2% N 5.47% O 6.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

Compound can be prepared in two different ways both starting from 2,6-xylidine (I): 1) By condensation of (I) with N-carbobenzoxyalanine (B) by means of dicyclohexylcarbodiimide in methylenechloride giving N-(carbobenzoxyalanyl)xylidine (II), which is then hydrogenated over Pd/C in ethanol - methylene chloride. 2) By condensation of (I) with 2-bromopropionyl bromide (A) by means of sodium acetate in acetic acid giving 2-bromo-2',6'-propionoxylidide (III), which is then treated with NH3 in alcohol water.

参考文献中间体

合成目标

【1】 Boyes, R.N.; et al.; Propionamide derivative a method of making it and therapeutic compositions containing it. DE 2235745; FR 2147277; GB 1374367; NL 7210418 .
【2】 Boyes, R.N.; et al.; Primary amino acylanilides methods of making the same and use as antiarrhythmic drugs. DE 2400540; ES 422085; FR 2213065; GB 1461602; JP 49116034 .
【3】 Hillier, K.; Castaner, J.; Tocainide. Drugs Fut 1977, 2, 2, 141.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	13127	2-Bromopropionyl bromide; 2-Bromopropanoyl bromide	563-76-8	C₃H₄Br₂O	详情	详情
(B)	61217	CBZ-DL-Alanine; 2-[[(Benzyloxy)carbonyl]amino]propionic acid; N-((Phenylmethoxy)carbonyl)-DL-alanine; Carbobenzyloxy-DL-alanine	4132-86-9	C₁₁H₁₃NO₄	详情	详情
(I)	17527	2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine	87-62-7	C₈H₁₁N	详情	详情
(II)	33595	benzyl 2-(2,6-dimethylanilino)-1-methyl-2-oxoethylcarbamate		C₁₉H₂₂N₂O₃	详情	详情
(III)	33594	2-bromo-N-(2,6-dimethylphenyl)propanamide		C₁₁H₁₄BrNO	详情	详情

Extended Information