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

HRID 1419348Notes

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-fb0e0785a4e947fba64250134f890ddb
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05886044

Reaction notes

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