Phenyl isocyanate → HCID 15411482, compound

HRID 1385330Notes

Reaction equation

HRID 1385330 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([OH:11])[CH:5]=1.[C:13]1([N:19]=[C:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[OH:11][C:6]1[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:12])[CH:9]=[CH:8][C:7]=1[NH:10][C:20]([NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21]

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 15411482HCID 15411482, compoundYield 90.7%

Procedure

N-[2-Hydroxy-4-(methoxycarbonyl)phenyl]-N′-phenyl urea was prepared from methyl-4-amino-3-hydroxybenzoate (200 mg, 1.19 mmol) and phenyl isocyanate (1.19 mmol) according to the procedure noted above in General Method A. The product was purified by precipitation from toluene, and filtering, to afford the titled compound (309 mg, 90%). mp: 188.4-188.8° C.; 1H NMR (CD3OD/CDCl3): d 8.15 (d, 1H, J=8.25 Hz), 7.70 (s, 1H), 7.51 (d, 1H, J=8.25 Hz), 7.43 (d, 2H, J=8.25 Hz), 7.30 (t, 2H, J=8.25 Hz), 7.01 (t, 1H, J=8.25 Hz), 3.87 (s, 3H); EI-MS m/z 286 (M+H)+; Anal. (C15H14N2O4) C, H, N.

Workup

  1. customThe product was purified by precipitation from toluene
  2. filtrationfiltering

Sources & evidence

ORD record
ord-7f46187f45dd45c6b8d979f0f58d21cd
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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