Phenyl isocyanate → HCID 15411482, compound

HRID 1956615Notes

Reaction equation

HRID 1956615 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); El-MS m/z 286 (M+H)+ ; Anal. (C15H4N2O4) C, H, N.

Workup

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

Sources & evidence

ORD record
ord-a5ceb723ffda471f81a7cee19037f32c
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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