Tetrahydrofuran → HCID 67151220, compound

Participants

Reaction Conditions

Reaction Steps

3,4-diamino-5-chlorobenzoate (from acid preparation 1, 100 mg, 0.50 mmol) and carbonyl diimidazole (89 mg, 0.55 mmol) were combined in tetrahydrofuran (2 mL) and stirred for 16 hours. The reaction solution was heated to 60° C. for 3 hours. To the reaction was added carbonyl diimidazole (81 mg, 0.50 mmol) and the reaction was continued at 60° C. for two hours. The reaction was allowed to cool to room temperature and stirred for 16 hours. A precipitate formed. The mixture was filtered. The filtrate was concentrated in vacuo and the residue was slurried in ethyl acetate. The slurry was filtered on the same filter as the original filtration. The collected solids were washed with a portion on ethyl acetate and then dried under a stream of nitrogen to give methyl 7-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate as a white solid (93 mg, 82%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.60 (br. s., 1 H) 11.16 (s, 1 H) 7.55 (d, J=1.37 Hz, 1 H) 7.38 (d, J=1.56 Hz, 1 H) 3.80 (s, 3 H).

Provenance & Evidence