تفاعل #73652

معادلة التفاعل

hydrochloric acid

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

sodium azide

ammonium chloride

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title compound

المردود 23.0%

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

المردود 23.0%

المذيبات

N,N-dimethylformamide

brine

Ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to ambient temperature
2. 2
   أخرىThe organic layer was separated
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزThe filtrate was concentrate in vacuo
6. 6
   أخرىthe residue was purified by column chromatography

الإجراء التجريبي

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).

المصدر