反应详情

A stirred suspension of 2-cyanoacetamide (790 mg, 9.4 mmol) in absolute ethanol (40 ml) was treated with sodium methoxide (495 mg, 9.2 mmol) and refluxed 10 minutes. The mixture was cooled lightly, a solution of 4-chloro-3-cyanobenzyl azide (1.35 g, 7.0 mmol) in absolute ethanol was added, an the mixture was refluxed 2.5 hours. The mixture was filtered hot and the filtrate evaporated under vacuum. The residue was triturated with diethyl ether, filtered, and washed twice with diethyl ether. The solid was crystallized from refluxing methanol, filtered, washed twice with methanol and once with diethyl ether, and dried at 65° C. under vacuum to provide 635 mg (33%) 5-amino-1-(4-chloro-3-cyanobenzyl)-1,2,3-triazole-4-carboxamide, m.p. 172°-175° C.

1. temperaturerefluxed 10 minutes
2. temperatureThe mixture was cooled lightly
3. temperaturean the mixture was refluxed 2.5 hours
4. filtrationThe mixture was filtered hot
5. customthe filtrate evaporated under vacuum
6. customThe residue was triturated with diethyl ether
7. filtrationfiltered
8. washwashed twice with diethyl ether
9. customThe solid was crystallized
10. temperaturefrom refluxing methanol
11. filtrationfiltered
12. washwashed twice with methanol and once with diethyl ether
13. customdried at 65° C. under vacuum