Methyl chloroformate → 2-(2,4-Dichlorophenyl)-3-(N,N-dimethoxycarbonylcarbamoyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol

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Reaction Steps

3-Carbamoyl-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (0.94 g., 3 mmole) was added to a suspension of oil-free sodium hydride (0.14 g., 5.8 mmole) in dry tetrahydrofuran (10 ml). The suspension was stirred for one hour and then a solution of methyl chloroformate (0.6 g., 6.3 mmole) in dry tetrahydrofuran (10 ml) was added dropwise over 15 minutes. The mixture was stirred at room temperature for three hours and then the solvent was evaporated in vacuo. The residue was partitioned between saturated aqueous sodium bicarbonate solution (10 ml) and ethyl acetate (40 ml), and the organic phase was separated, washed with brine (10 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica eluting with ethyl acetate/methanol 95:5 (v:v), and the fractions containing the product were combined and evaporated and recrystallized from ethyl acetate-hexane to give the title compound, (62 mg, 5%), m.p. 155°-156° C.

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