Hydrochloric Acid → HCID 178507270, compound

Participants

Reaction Steps

To a flask charged with 600 mL of absolute ethanol was dissolved sodium (14.86 g, 646.5 mmol) with a catalytic amount of copper(II)sulfate (10 mg). The reaction volume was reduced by half under reduced pressure and thiourea (49.22 g, 646.5 mmol) and 3-amino-3-(4-bromophenyl)acrylonitrile (38.46 g, 172.4 mmol) were added at ambient temperature and the reaction mixture was fitted with a condenser and heated to reflux over the weekend. Water (400 mL) was added and the mixture was made acidic with concentrated aqueous hydrochloric acid to a pH=7. The reaction mixture was allowed to stir for 5 minutes and the resulting solids were collected by means of vacuum filtration and afforded 6-amino-4-(4-bromophenyl)pyrimidine-2(1H)-thione (53.90 g, 191.0 mmol, 110.8% yield). MS (apci) m/z=282.0 (M+H).

Provenance & Evidence