Ammonia → HCID 10845577, compound

Participants

Reaction Steps

Calcium turnings (3.5 g) were added portionwise to liquid ammonia (500 ml) and the whole was stirred vigorously for 10 min. The thioacetal from step b) (10 g) in ether (7 ml) was added dropwise to the dark blue solution over a 7 min period. The mixture was stirred for 2 hours and then quenched with ammonium chloride until effervescing had ceased. Excess ammonia was allowed to evaporate by purging under nitrogen overnight. The remaining solid was acidified using dilute 10% aqueous hydrochloric acid to pH 1-2 and the product extracted with ethyl acetate. The organic layers were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give the subtitled compound (8.29 g).

Provenance & Evidence