Water → HCID 2954358, compound

Participants

Reaction Steps

A solution of 4-nitrophenylisocyanate (2.17 g, 12.83 mmol) in anhydrous DCM (15 ml) was added dropwise to a stirred suspension of dimethyl 5-aminoisophthalate (7.23) (2.71 g, 12.83 mmol) in DCM (35 ml). The reaction mixture was stirred for 1 h under an inert atmosphere after which it was diluted with ethyl acetate (100 ml) to dissolve a yellow precipitate which had formed during the reaction. This gave a yellow solution which formed a white precipitate on addition of water (30 ml). The precipitate was collected by filtration, repeatedly washed with water, and dried under reduced pressure. This gave a white solid which was recrystallised from acetone/petrol 40-60 to give the title compound 7.67 as a white powder (2.53 g, 53%). M.p. 193°-195° C.; m/z (+EI) 748 (5%, 2M+H+), 374 (100%, M+H+), 373 (32%, M), 342 (35%, M+H+-OMe); δH (250 MHz, d6 -DMSO) 3.85 (s, 6H, 2×OCH3), 7.70 (2H, d, J 7.5 Hz, 2×Ar--H), 8.10 (1H, s, Ar--H), 8.25 (2H, d, J 7.5 Hz, 2×Ar--H) 8.40 (2H, s, Ar--H), 9.50 (1H, s, NH), 9.55 (1H, s, NH); δC (62.5 MHz, CD3OD) 52.96. 118.28, 123.40, 123.65, 131.13, 140.65, 141.73, 146.43, 152.41, 165.74; RF 0.19 [DCM/methanol (95:5)].

Provenance & Evidence