Methyl 4-aminobenzoate → 766556-60-9

Participants

Reaction Steps

Methyl 4-aminobenzoate (3.0 g, 20.0 mmol) and 1-chloro-3-isocyanato-propane (2.0 mL, 20.0 mmol) were stirred in THF (50 mL) at room temperature overnight. The solvents were evaporated. A THF (50 mL) solution of the residue (5.0 g, 18.51 mmol) was added to a stirred solution of NaH (60%, 0.93 g, 23.25 mmol) in THF (60 mL) portionwise at room temperature. The mixture was stirred for 3.5 h. It was evaporated. H2O was added. It was extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated to dryness to give pure 4-(2-oxo-tetrahydro-pyrimidin-1-yl)-benzoic acid methyl ester as a white solid (2.15 g, yield: 49.6%). 1H NMR (DMSO-d6) δ 7.88 (d, J=8.5 Hz, 2H), 7.48 (d, J=8.6 Hz, 2H), 6.82 (s, br, 1H), 3.68 (m, 2H), 3.34 (s, 3H), 3.23 (m, 2H), 1.96 (m, 2H) ppm. LC-MS (ESI) 235.23 (M+H), tR=2.17 min (10–90% MeOH in H2O in a 4-min run).

Provenance & Evidence