Acetic Anhydride → HCID 86026439, compound

Participants

Reaction Conditions

Reaction Steps

Diamine 3 (200 mg, 1.14 mmol) and maleic anhydride (335 mg, 3.42 mmol) were placed in a dry 50-mL round bottom flask. Chloroform (11.5 mL) was added and the solution was heated to reflux for 20 h. The mixture was then filtered and the recovered solid was rinsed liberally with chloroform and then dried under vacuum. To this solid was added acetic anhydride (9 mL, 96 mmol) and sodium acetate (35 mg, 0.427 mmol) and the reaction was stirred vigorously for another 30 min. The mixture was then cooled to 4° C. for 4 h and filtered. The beige solid thus obtained was dried over vacuum to give compound 4 in 20% yield (76 mg, 0.226 mmol). mp: >296° C. (dec). FTIR (KBr) (cm−1): 1700, 1620. 1H-NMR (CDCl3): δ (ppm) 7.78 (s, 1H), 7.66 (dd, J=9.8 Hz, J=2.5 Hz, 1H), 7.63 (d, J=2.5 Hz, 1H), 7.50 (d, J=8.7 Hz, 1H), 6.93 (s, 2H), 6.91 (s, 2H). 13C-NMR (DMSO-d6): δ (ppm) 1699.99, 169.06, 156.80, 151.50, 143.62, 135.82, 134.89, 131.61, 128.63, 127.11, 118.60, 118.13, 117.58. HRMS: expected, 337.04630; found, 337.04605.

Provenance & Evidence