2H-Benzimidazol-2-one,1,3-dihydro-4-methoxy-(9CI) synthesis

Yield:-

Reaction Conditions:

with diphenyl phosphoryl azide;triethylamine in tetrahydrofuran at 80;

Steps:

209.4

To a round bottomed flask was added 2-amino-3-methoxybenzoic acid (2.2705 g, 13.58 mmol), diphenyl phosphorazidate (3.51 mL, 16.30 mmol), and triethylamine (3.79 mL, 27.2 mmol) in THF to stir at 80 ⁰C. Upon completion the reaction was allowed to cool to room temperature. Solvent was evaporated. The residue was taken up in DCM. The reaction mixture was diluted with water and extracted with DCM. A white precipitate was noted to form during extraction The solid was filtered to provide 4-methoxy-lH-benzo[d]imidazol-2(3H)-one. [M+H] = 165.0.

References:

WO2010/57121,2010,A1 Location in patent:Page/Page column 188