Dichloromethane → HCID 131714707, compound

Participants

Reaction Steps

Dinitrogen trioxide gas (1.5 g) was introduced into a solution of the thus prepared 3-isopentyl-3-(n-butyl-α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (4.68 g, 11.38 mmol) in a mixture of dichloroethane (50 ml), dichloromethane (10 ml), and monochlorobenzene (10 ml) with thorough stirring at 10°-18° C., and stirring was continued for further one hour at the same temperature. The reaction mixture was vacuum-concentrated at 28° C. or below and purified by column chromatography (packing silica gel; eluent: octane/isopropyl acetate 4:1) to obtain 3-isopentyl-3-(n-butyl-α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea (3.82 g, 8.68 mmol); yield 76.3%; m.p. 66°-68° C.; [α]D20 +65.3° (C 1.0, methanol).

Provenance & Evidence