反应详情

A stirred suspension of 2-cyanoacetamide (378 mg, 4.50 mmol) in ethanol (15 ml) was treated with sodium methoxide (236 mg, 4.37 mmol), refluxed 10 minutes, cooled slightly, and treated with 4-(4-chlorobenzoyl)-3-chlorobenzyl azide (1.03 g, 3.36 mmol) dissolved in ethanol (4 ml). The mixture was refluxed 2 hours, cooled to ambient temperature, and filtered. The solids were washed with ethanol, and the combined filtrate and wash were evaporated to dryness under vacuum. The residue was dissolved in 19:1 (v/v) dichloromethane-methanol (40 ml) and chromatographed on a column of silica gel (60 g) eluted in 20 ml fractions with 97:3 (v/v) dichloromethane-methanol. Fractions 15-42 were combined and evaporated under vacuum to provide 402 mg (32%) of 5-amino-1-(4-[4-chlorobenzoyl]-3-chlorobenzyl)-1,2,3-triazole-4-carboxamide, m.p. 203°-205° C.

1. temperaturerefluxed 10 minutes
2. temperaturecooled slightly
3. temperatureThe mixture was refluxed 2 hours
4. filtrationfiltered
5. washThe solids were washed with ethanol
6. washthe combined filtrate and wash
7. customwere evaporated to dryness under vacuum
8. dissolutionThe residue was dissolved in 19:1 (v/v) dichloromethane-methanol (40 ml)
9. customchromatographed on a column of silica gel (60 g)
10. washeluted in 20 ml fractions with 97:3 (v/v) dichloromethane-methanol
11. customevaporated under vacuum