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

HRID 323019Notes

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

Reactant 2

HCID 7672Phenyl isocyanate

HCID 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

customThe product was purified by precipitation from toluene
filtrationfiltering

Sources & evidence

ORD record: ord-5edbe52176554a44a57ab66c5182c159
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211373B1

Reaction notes

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