Aniline → HCID 4592636, compound

Participants

Reaction Steps

A solution of 2,2,3,3-tetramethylcyclopropanecarbonyl chloride (1.60 g, 10 mmole) in CH2Cl2 (5 ml) was added dropwise to a solution of aniline (2.8 g, 30 mmole) in CH2Cl2 (10 ml), while maintaining the temperature at 10°-20° C. The reaction mixture was stirred for 6 hours at room temperature, diluted with CH2Cl2 (15 ml) and washed successively with H2O (2×10 ml), 1N HCl (2×10 ml), H2O (20 ml) saturated NaCl (2×15 ml). The organic layer was separated, dried over MgSO4, and evaporated to dryness under reduced pressure. The residue was crystallized from EtOAc/hexane to afford 1.1 g (5.07 mmole, 51%) of a white crystalline solid), m.p. 149° C.

Provenance & Evidence