Methanol → HCID 58183758, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 68.3 g (0.35 mol) of (p-toluenesulfonyl)methyl isocyanide (TOSMIC) in 300 ml of dimethoxyethane was added dropwise to a stirred suspension of 78 g (0.70 mol) of potassium tert-butoxide in 300 ml of dimethoxyethane at −30° C. under nitrogen. After the solution had been cooled to −55° C., a solution of 92 g (0.34 mol) of 4-(N,N-diphenylamino)benzaldehyde in 100 ml of dimethoxyethane was added dropwise. After stirring at −55° C. for 1 hour, methanol was added. The reaction solution was heated to boiling under reflux for 30 min. After the solution had been concentrated to dryness, the residue was taken up with 600 ml of water and 30 ml of acetic acid. The aqueous solution was extracted with methylene chloride. The combined organic phases were washed with a saturated sodium carbonate solution, dried over magnesium sulfate and concentrated to dryness. 75 g (79% of theory) of the desired nitrile were obtained.

Provenance & Evidence