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

HRID 612627Notes

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

Reactant 2

HCID 7672Phenyl isocyanate

HCID 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): δ 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

customThe product was purified by precipitation from methylene chloride
filtrationfiltering

Sources & evidence

ORD record: ord-96dd645da7984f2caf6d7bb2c9979383
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06005008

Reaction notes

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