Ammonia → HCID 13881505, compound

Participants

Reaction Steps

A solution of 0.75 g (7.1 mmoles) of cyanogen bromide in 10 ml of n-butanol is added dropwise, within about 0.5 hours, to a stirred solution of 2.0 g (7.1 mmole) of 1,3-bis(2',6'-dimethylphenyl-amino)-propane in 20 ml of n-butanol at 110° to 115° C. After the addition the mixture is stirred for further 2 hours at the same temperature. Thereafter the mixture is cooled, shaken five times with 10 ml of water each, the aqueous solutions are combined, and the pH of the mixture is adjusted to 8.0 to 8.5 with concentrated aqueous ammonia. The separated unreacted starting substance (0.4 g, m.p.: 68°-71° C.) is filtered off, the aqueous filtrate is rendered alkaline with 2 n aqueous sodium hydroxide solution, and the aqueous-alkaline phase is extracted thrice with 30 ml of chloroform each. The organic phases are combined, washed with water, dried over potassium carbonate, and the solvent is distilled off. 0.8 g (36.7%) of 1,3-bis(2',6'-dimethylphenyl)-2-imino-hexahydro-pyrimidine are obtained; m.p.: 181°-183° C. (after recrystallization from aqueous isopropenol).

Provenance & Evidence