反应详情

Ethyl 4-(1,2,4-triazol-1-yl)benzoate (520 mg, 2.4 mmol) was heated at reflux in 5N HCl (40 ml) for 1 h, and the product filtered off and dried in vacuo to afford the acid (88%). 4-(1,2,4triazol-1-yl)benzoic acid (0.395 g, 2.1 mmol) was suspended in dry toluene (40 ml) and thionyl chloride (2 ml) added under argon. The mixture was heated to reflux for 1.5 h and then evaporated to dryness under reduced pressure. The oil was dissolved in dichloromethane under argon and 4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine (460 mg, 2.1 mmol) was added followed by triethylamine (2 ml). The mixture was stirred at room temperature under argon for 2 h and then partitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml), and the organic extracts dried (sodium sulphate). The organic solution was filtered, evaporated to dryness under reduced pressure and purified by column chromatography (silica, chloroform/methanol 5-10%) to afford the amide (757 mg, 92%) which was crystallised from methanol diethyl ether as the oxalate salt.

1. temperatureThe mixture was heated
2. temperatureto reflux for 1.5 h
3. customevaporated to dryness under reduced pressure
4. dissolutionThe oil was dissolved in dichloromethane under argon
5. custompartitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml)
6. dry with materialthe organic extracts dried (sodium sulphate)
7. filtrationThe organic solution was filtered
8. customevaporated to dryness under reduced pressure
9. custompurified by column chromatography (silica, chloroform/methanol 5-10%)