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

HRID 567960Notes

Reaction equation

HRID 567960 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′-phenylurea 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): δ 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-d44577db479c4013a8b440e47e7a4360
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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