Ammonia → HCID 86629666, compound

Participants

Reaction Steps

Add thionyl chloride (1.35 mL, 18.4 mmol) to a mixture of 4-cycloheptylthio-benzoic acid (984 mg, 3.93 mmol) in dichloromethane (15 mL) at 0° C. Heat the mixture to reflux for 1 h. Cool the mixture to room temperature and concentrate in vacuo. Dissolve the residue in dichloromethane (20 mL) and cool to 0° C. Add triethylamine (1.1 mL, 7.86 mmol) and bubble ammonia gas through the solution Warm the mixture to room temperature and stir for 1 h. Dilute with water (20 mL) and extract the aqueous phase with dichloromethane (3×20 mL). Wash the combined organic extracts with saturated aqueous NaHCO3 (20 mL). Dry the organic solution over Na2SO4, filter and concentrate in vacuo to provide the desired intermediate as an off-white solid (976 mg, 99%). MS (APCI) m/z: 250 (M+H)+.

Provenance & Evidence