Triethylamine → 4-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

Participants

Reaction Steps

To a stirred mixture of 4-aminophenylacetic acid (15.0 g) and o-tolylisocyanate (10.2 ml) in CH2Cl2 (200 ml) was added triethylamine (13.8 ml). After 1 h the resulting homogeneous solution was concentrated under reduced pressure, dissolved in water (100 ml) and acidified to pH 2 with 1N HCl. The off-white ppt was filtered, suspended in THF (200 ml) and 10 ml conc. HCl was added. The resulting homogeneous solution was concentrated under reduced pressure and recrystallized from EtOAc (800 ml) to give 22 g of the title compound as a white solid. MP 221-2° C.; MS [M+1]+ 285.2; Analysis calcd. for C16H16N203: C (67.59), H (5.67), N (9.85). Found: C (67.22), H (5.78), N (9.69).

Provenance & Evidence