2-Methoxyethylamine → N-(2-Hydroxy-4-nitrophenyl)-N'-(2-methoxyethyl)urea

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-tert-butyldimethylsilyloxy-4-nitroaniline (200 mg, 0.75 mmol) in toluene (5 mL), triphosgene (84 mg, 0.3 mmol) and triethylamine (0.13 mL, 0.9 mmol) were added. The reaction mixture was stirred at 80° C. for 3 hours. Then it was cooled to room temperature and all solvent was evaporated. The residue was dissolved in DMF (1 mL) and 2-methoxyethylamine (56.3 mg, 0.75 mmol) was added. The reaction mixture was stirred at 80° C. for 16 hours. Chromatography of the resulting liquid on silica gel (50% Ethyl acetate/Hexane) gave desired product (95 mg, 50%). EI-MS m/z 256.2 (M+). mp: 190.0-190.7° C.

Provenance & Evidence