Methyl bromoacetate → HCID 54122834, compound

Participants

Reaction Steps

A mixture of 4-methyl-1-phenylsemicarbazide (20.0 g), methyl bromoacetate (27.75 g) and diisopropylethylamine (23.2 ml) in toluene (200 ml) under nitrogen was heated at 90° to 100° for 25 h with stirring. Toluene (120 ml) was then distilled off at ca. 90° under reduced pressure. The mixture was cooled to <50° and diluted with water (120 ml) and ethyl acetate (200 ml). The organic phase was separated and washed with water (60 ml). The two aqueous phases were extracted sequentially with ethyl acetate (2×60 ml). The combined organic phases were filtered and concentrated to 80 ml at atmospheric pressure. Toluene (100 ml) was added and the solution was again concentrated to 80 ml. The concentrate was seeded at ca. 80° with an authentic sample of the title compound, and allowed to cool to ca. 20° overnight. The resultant solid was filtered off, washed with toluene (20 ml) followed by t-butyl methyl ether (20 ml), and dried in vacuo for 24 h to give the title compound (22.39 g), m.p. 122°-122.5°.

Provenance & Evidence