Acetone → benzyl N-(2-bromoethyl)carbamate

Participants

Reaction Steps

A solution of 0.46 mol (78.5 g) of benzyloxycarbonyl chloride in 1 volume of acetone is added slowly to a solution of 0.45 mol (92.2 g) of 2-bromoethylamine in 1 liter of nomal sodium hydroxide solution. When the reaction has ended (about 48 hours), the acetone is evaporated off under reduced pressure and the residue is then acidified to between pH 1 and 2 and extracted with ether. Benzyloxycarbonylamino-2-bromoethane is obtained after evaporation. This product is reacted with N-hydroxyphthalimide following the procedure of Example 1-a to give N-2-benzyloxycarbonylaminoethoxyphthalimide in the form of white crystals melting at 95° C. with a yield of 73%. After treatment with hydrazine under the conditions of Example 1-a, 2-benzyloxycarbonylaminoethoxyamine hydrochloride melting at 178° C. is obtained (yield=95% relative to the phthalimide).

Provenance & Evidence