Dichloromethane → HCID 67531839, compound

Participants

Reaction Steps

To a 100 mL round-bottomed flask equipped with a magnetic stir bar was added tert-butyl 6-amino-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate (0.142 g, 0.317 mmol), dichoromethane (10 mL) and isobenzofuran-1,3-dione (0.047 g, 0.317 mmol). The stirring solution was allowed stir for 24 hours at room temperature. Volatiles were evaporated under reduced pressure. The resulting residue was dissolved up in a 1:1:2 mixture of concentrated HCl, H2O and THF (10 mL) and allowed to stir for seven hours with ventilation. Volatiles were then evaporated under reduced pressure. The resulting solid was rinsed thoroughly with ether providing the title compound (0.083 g, 81% yield) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.95 (d, 1H), δ 7.71 (m, 2H), δ 7.59 (m, 2H), δ 7.47 (m, 1H), δ 7.30 (t, 1H) ppm; 13C NMR (75 MHz, CD3OD) δ 170.1, 132.9, 130.9, 130.2, 128.6, 126.5, 123.4, 118.2, 117.8, 112.1 ppm; HRMS (ESI) Calcd for C15H12N4O2 (M+) 296.0909. Found 296.0915.

Provenance & Evidence