Toluene → HCID 67664036, compound

Participants

Reaction Steps

21 (100 mg, 0.33 mmol) was added to a solution of methyl(triphenylphosphoranylidene)acetate (120 mg, 0.36 mmol) in toluene (30 mL) and the reaction mixture was heated to reflux for 4 days. The solvent was removed after cooled to room temperature. The product was crystallized in a solution of acetone and ether. The mother liquid was then purified by flush column chromatography eluting with ethyl acetate and hexane (1/2, v/v). A total of 78 mg (66% yield) of yellow solid 22 was obtained. mp: 259°-260° C. 1H NMR (DMSO-d6, ppm): 11.57 (s, 1 H, NH), 10.38 (s, 1 H, NH), 8.07-7.35 (m, 9 H, Ar--H, CH=CH), 6.93 (s, 1 H, Ar--H), 6.57-6.53 (d, 1 H, J=15.8 Hz, CH=CH), 3.74 (s, 3 H, CH3). Anal. (C21H16N2 O4), C, H, N.

Provenance & Evidence