Hydrochloric Acid → HCID 19822112, compound

Participants

Reaction Steps

A solution of triphenylphosphine (2.35 g, 9 mmol) in anhydrous tetrahydrofuran (30 ml) was treated dropwise with diethyl azodicarboxylate (1.4 ml, 9 mmol) over 5 min at 0° C. The solution was stirred at this temperature for 30 min and ten treated with a solution of 2-hydroxy-2,N-dimethyl-1-(pyrid-3-yl)cyclohexane carbothioamide (1.59 g, 6 mmol) in anhydrous tetrahydrofuran (15 ml). The mixture was warmed to room temperature and stirred for 16 h. The solution was then poured into aqueous hydrochloric acid (0.5 M, 60 ml) and extracted with ethyl acetate (3×45 ml). The aqueous phase was basified with 2 M aqueous sodium carbonate solution and extracted with dichloromethane (3×45 ml). The organic extract was dried over magnesium sulphate and evaporated to give a pale brown oil This was subjected to flash chromatography over silica gel, eluting with ethyl acetate/methanol (98:2) to give (±)-2-methylene-N-methyl-1-(pyrid-3-yl)cyclohexane carbothioamide (0.25 g) as a colourless solid, m.p. 106.5°-108.5° C.;

Provenance & Evidence