Ammonia → HCID 19864114, compound

Participants

Reaction Steps

25.3 g of sodium borohydride in 435 ml of 1,2-dimethoxyethane are placed under a nitrogen atmosphere. 36.9 ml of titanium tetrachloride are added dropwise thereto at a temperature of from +15° to +18° C. The mixture is stirred for 3 hours at a temperature below +20° C. and then, at from +14° to +16° C., a solution of 33.0 g of 3,3-dimethylisothiochroman-4-oneoxime in 135 ml of 1,2-dimethoxyethane is added dropwise thereto. After stirring for 16 hours at room temperature, the mixture is poured onto ice-water and rendered basic with 30% aqueous ammonia solution. The mixture is then extracted twice with ether. The ether phases are washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation. Distillation of the residue yields 16.7 g of 4-amino-3,3-dimethylisothiochroman in the form of a colourless liquid having a boiling point of +80° C. at 0.06 mbar.

Provenance & Evidence