Phenyl isocyanate → n-[2-Hydroxy-4-(trifluoromethyl)phenyl]-n'-phenylurea

HRID 1385337Notes

Reaction equation

HRID 1385337 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[OH:12].[C:13]1([N:19]=[C:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[OH:12][C:3]1[CH:4]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:6]=[CH:7][C:2]=1[NH:1][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 155242772-Amino-5-(trifluoromethyl)phenol

Product 1

HCID 15411485n-[2-Hydroxy-4-(trifluoromethyl)phenyl]-n'-phenylureaYield 87%

Procedure

N -[2-Hydroxy-4-(trifluoromethyl) phenyl]-N′-phenyl urea was prepared from 2-amino-5-trifluoromethylphenol (150 mg, 1.09 mmol) and phenyl isocyanate (1.09 mmol) according to the procedure in General method A. The product was purified by precipitation from methylene chloride and filtering to afford the titled compound (230 mg, 87% ). mp: ° C.; 1H NMR (DMSO-d6): d 9.45 (s, 1H, NH), 8.50 (s, 1H, NH), 8.31 (d, 1H, J=10.0 Hz), 7.45 (d, 2H, J=10.0 Hz), 7.29 (t, 2H, J=6.67 Hz), 7.10 (m, 2H), 6.99 (t, 1H, J=6.67 Hz). EI-MS m/z 296 (M+). Anal. (C14H11N2O2F3)C, H, N.

Workup

  1. customThe product was purified by precipitation from methylene chloride
  2. filtrationfiltering

Sources & evidence

ORD record
ord-fa7976c08bd44797a2203352987af787
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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