4-CHLORO-N-(1,3-THIAZOL-2-YL)BUTANAMIDE synthesis

Yield:37762-99-5 92%

Reaction Conditions:

with potassium carbonate in toluene at 20; for 24 h;

Steps:

7.1.1. 4-Chloro-N-(thiazol-2-yl)-butanamide 7

A mixture of 2-aminothiazole (4, 4.0 g, 0.04 mol), 4-chlorobutyryl chloride (6, 11.3 g, 0.08 mol), and potassium carbonate (1.4 g, 0.01 mol) in toluene (100 ml) was stirred at room temperature for 24 h. The toluene was then evaporated under reduced pressure. The residue was then quenched with water, stirred, and filtered. The solid obtained was washed, dried and recrystallized from water to give the required product 7; 92% yield, mp 125-127 °C, ¹H NMR (CDCl₃): δ 12.92 (s, 1H, NH), 7.54 (d, 1H, J = 3.5 Hz, thiazole-H), 7.04 (d, 1H, J = 3.5 Hz, thiazole-H), 3.71 (t, 2H, J = 6.0 Hz, CH₂), 2.81 (t, 2H, J = 6.0 Hz, CH₂), 2.31-2.26 (m, 2H, CH₂). ¹³C NMR: δ 27.3, 32.8, 44.4, 113.6, 136.2, 160.1, 170.0. MS: m/z 113 (100%), M = 204 (20%), M + 2 = 206 (5%). (C₇H₉ClN₂OS) C, H, N.

References:

El-Subbagh, Hussein I.;Hassan, Ghada S.;El-Azab, Adel S.;Abdel-Aziz, Alaa A.-M.;Kadi, Adnan A.;Al-Obaid, Abdulrahman M.;Al-Shabanah, Othman A.;Sayed-Ahmed, Mohamed M. [European Journal of Medicinal Chemistry,2011,vol. 46,# 11,p. 5567 - 5572] Location in patent:experimental part