Oxalyl chloride → HCID 9902489, compound

Participants

Reaction Steps

A solution of 4-cyclohexyl-benzoic acid (0.479 g) in tetrahydrofuran (10 ml) was treated with N,N-dimethylformamide (20 μl) followed by dropwise addition of oxalyl chloride (0.260 ml). When the gas evolution stopped the solution was warmed to reflux for 5 minutes, then cooled and concentrated in vacuo to an oil. The oil was diluted with tetrahydrofuran (5 ml) and again concentrated in vacuo. This cycle was repeated one more time and then the oil was dissolved in dichloromethane (15 ml). A solution of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine (0.300 g) and Hunig's base (1.1 equiv.) in dichloromethane (25 ml) was cooled to 0° and treated dropwise with the previously prepared solution of 4-cyclohexylbenzoyl chloride. The reaction was stirred overnight as the temperature was allowed to return to room temperature. The solution was washed sequentially with 0.1N hydrochloric acid, 50% saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residual oil was flash chromatographed on silica gel using 15% ethyl acetate in hexanes as the eluant to provide the title compound (0.54 g) as an orange tinged solid.

Provenance & Evidence