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

HRID 1419344Notes

Reaction equation

HRID 1419344 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): δ7.70 (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. customwas purified by precipitation from toluene
  2. filtrationfiltering

Sources & evidence

ORD record
ord-9e9a1c00e1264967aec5e2bf4c8f8ae6
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

Loading…