반응 #73652

반응 방정식

hydrochloric acid

2-(4-cyanobenzoylamino)-4-methylthiazole-5-carboxylic acid benzylamide

sodium azide

ammonium chloride

→

title compound

수율 23.0%

4-Methyl-2-[4-(2H-tetrazol-5-yl)benzoylamino]thiazole-5-carboxylic Acid Benzylamide

수율 23.0%

용매

N,N-dimethylformamide

brine

Ethyl acetate

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to ambient temperature
2. 2
   기타The organic layer was separated
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   여과filtered
5. 5
   농축The filtrate was concentrate in vacuo
6. 6
   기타the residue was purified by column chromatography

실험 절차

A mixture of 2-(4-cyanobenzoylamino)-4-methylthiazole-5-carboxylic acid benzylamide (0.080 g, 0.21 mmol), sodium azide (0.028 g, 0.43 mmol) and ammonium chloride (0.006 g, 0.11 mmol) in N,N-dimethylformamide (5 mL) was stirred at 80° C. for 18 hours. The reaction mixture was cooled to ambient temperature, and 1 N hydrochloric acid (0.5 mL) solution was added. Ethyl acetate (10 mL) and brine (10 mL) were added to the reaction mixture. The organic layer was separated and dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrate in vacuo and the residue was purified by column chromatography to afford the title compound as a white solid in 23% yield (0.020 g); m.p.>300° C.; 1H NMR (CD3OD, 300 MHz) δ 8.20-8.09 (m, 4H), 8.45-7.20 (m, 5H), 4.51 (s, 2H), 2.55 (s, 3H); 13C NMR (CD3OD, 75 MHz) δ 163.6, 138.8, 128.4, 128.1, 127.1, 126.8, 126.5, 43.1, 15.8; MS (ES+) m/z 420.5 (M+1).

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