ChemicalBook CAS DataBase List 2-(CHLOROMETHYL)-4-(4-NITROPHENYL)-1,3-THIAZOLE

2-(CHLOROMETHYL)-4-(4-NITROPHENYL)-1,3-THIAZOLE synthesis

5synthesis methods

Product Name:2-(CHLOROMETHYL)-4-(4-NITROPHENYL)-1,3-THIAZOLE
CAS Number:89250-26-0
Molecular formula:C10H7ClN2O2S
Molecular Weight:254.69

ETHYL 4-(4-NITROPHENYL)-1,3-THIAZOLE-2-CARBOXYLATE

53101-04-5
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2-(CHLOROMETHYL)-4-(4-NITROPHENYL)-1,3-THIAZOLE

89250-26-0
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Yield:-

Reaction Conditions:

Stage #1: ethyl 4-(4-nitrophenyl)-1,3-thiazole-2-carboxylatewith sodium tetrahydroborate in ethanol at 20; for 0.5 h;
Stage #2: with thionyl chloride in N,N-dimethyl-formamide; for 1 h;Reflux;

Steps:

3-(Chloromethyl)-5-methyl-1-phenyl-1H-pyrazole (13c)

General procedure: In a solution of intermediate 9 (92.1 mg, 0.40 mmol)dissolved in ethanol (5 mL), sodium borohydride (19.0 mg, 0.50 mmol) was added. The mixture wasstirred at room temperature for 30 min, and then water was added. The solution was extractedwith ethyl acetate, and the combined organic layers were washed with water and brine, driedover Na2SO4, and concentrated in vacuo. The residue was dissolved in DMF (2 mL); then thionylchloride (0.10 mL, 1.4 mmol) was added. After reux for 1 h, water was added and extractedwith ethyl acetate. The combined organic layers were washed with water and brine, dried overNa2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel(petroleum ether:ethyl acetate = 10:1) to give 13c (66.6 mg, 80.5%) as a white solid.

References:

Wang, Xinran;Lin, Xuehua;Xu, Xuanqi;Li, Wei;Hao, Lijuan;Liu, Chunchi;Zhao, Dongmei;Cheng, Maosheng [Molecules,2017,vol. 22,# 11,art. no. 1925]