Dichloromethane → 1-azido-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

Participants

Reaction Steps

A solution of sodium azide (22.75 g, 0.35 mole) in water (62.5 ml) was added to a solution of 2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane monomesylate (25 g, 0.068 mole) in dimethylformamide (DMF) (250 ml) and the reaction mixture was stirred at room temperature for 0.5 hours and then at 60° for 16 hours. The reaction mixture was cooled and then poured into a mixture of dichloromethane (250 ml) and water (75 ml). The two phases were separated and the aqueous phase was extracted with dichloromethane (2×25 ml) and the combined organic extracts were then dried (MgSO4), filtered and evaporated. The residue was triturated with diethyl ether and the resulting solid filtered off and then recrystallized from an ethyl acetate-hexane mixture to furnish the title azide as a colorless crystalline solid, (16.9 g, 79%) m.p. 117°-19°.

Provenance & Evidence