Acetamidine monohydrochloride → HCID 178467223, compound

Participants

Reaction Steps

In 500 ml of dioxane are added 83.5 g (0.50 mole) 2-chloro-1,1-dimethoxy-3-butanone, 94.5 g (1.0 mole) acetamidine hydrochloride and 123 g (1.5 mole) sodium acetate and the mixture is heated at reflux overnight. The cooled reaction mixture is filtered through a silica gel pad on a sintered glass filter funnel, washing with 3500 ml of dioxane. The filtrate and washings are combined and evaporated in vacuo to provide a residual oil which is purified by chromatography on a silica gel column (600 g), eluting with ethyl acetate. Fractions of 200 ml each are collected. After 16 fractions the elution is with 95:5 ethyl acetate/methanol. Fractions 18-35 are combined and the solvent evaporated in vacuo to afford 28.82 g (46.4%) of the desired product. Recrystallization from 1:1 ethyl acetate/isopropyl ether yields 19.27 g (31%) of crystals, M.P. 132°-133° C. Another 4.24 g (6.8%) was obtained by reworking the mother liquor. 1H-NMR (CD3OD) ppm (delta): 2.40 (s, 3H), 2.43 (s, 3H), 7.68 (s, 1H).

Provenance & Evidence