tert-Butyl(isothiocyanato)dimethylsilane → 3,8-Dimethyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide

Participants

Reaction Steps

A 1.55 molar solution of butyl lithium in hexane (12.9 ml, 20 mM) maintained below 10° was treated with a solution of 5,6,7,8-tetrahydro-3,8-dimethylquinoline (3.22 g, 20 mM) in tetrahydrofuran (10 ml). After 0.5 hours a 22% solution of t-butyldimethylsilyl isothiocyanate in benzene (13.7 g, 20 mM) was added dropwise. After a further 0.5 hours the reaction was quenched with water (100 ml.) then acidified (to pH1). After 1 hour the layers were separated, the aqueous layer basified (to pH9) and extracted with dichloromethane (2×50 ml). The organic extracts were dried and evaporated. Recrystallisation of the residue from toluene gave the title thioamide (3.3 g, 75%) mp. 160°-2°

Provenance & Evidence