Phenyl isocyanate → N-(2-hydroxy-4-fluorophenyl)-N'-phenylurea

HRID 1385333Notes

Reaction equation

HRID 1385333 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[OH:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:1][C:17]([NH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 1857632-Amino-5-fluorophenol

Product 1

HCID 15411484N-(2-hydroxy-4-fluorophenyl)-N'-phenylureaYield 91%

Procedure

N-(2-Hydroxy-4-fluorophenyl)-N′-phenyl urea was prepared from 2-amino-5-fluoro phenol (200 mg, 1.57 mmol) and phenyl isocyanate according to the procedure in General Method A. The product was purified by precipitation from toluene and filtering to afford the titled compound (352 mg, 91%). mp: 195.5-195.7° C.; 1H NMR (CD3OD/CDCl3): d 7.70 (m, 1H), 7.3 (d, 2H, J=8.25 Hz), 7.15 (t, 2H, J=8.25 Hz), 6.89 (t, 1H, J=8.25 Hz), 6.50-6.38 (m, 2H); EI-MS m/z 246 (M+H)+; Anal. (C13H11N2O2F) C, H, N.

Workup

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

Sources & evidence

ORD record
ord-c3c75265244e4ee58e04d8928edd1f52
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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