Dimethylformamide → 2-cyclohexylacetonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of the cyclohexylacetic acid (20.0 g, 141 mmol) in CH2Cl2 (80 mL) was heated to reflux and a solution of chlorosulfonyl isocyanate (20.9 g, 148 mmol) in CH2Cl2 (18 mL) was added dropwise over 40 minutes. After the addition was complete, stirring was continued at reflux for 65 minutes. The mixture was cooled to 0° C., and DMF (21.1 g, 288 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred 18 hours. The mixture was poured over ice, the organic layer separated, and the aqueous layer extracted with CH2Cl2 (50 mL). The combined organic layers were washed with water (3×50 mL), brine, dried (Na2SO4), filtered through a plug of Florosil and concentrated. The nitrile was obtained as 14.6 g (85%) of an oil of sufficient purity for use in the next reaction.

Provenance & Evidence