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

HRID 1956621Notes

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): 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 mz 296 (M+). Anal. (C14 H11N2O2F3)C, H, N.

Workup

customThe product was purified by precipitation from methylene chloride
filtrationfiltering

Sources & evidence

ORD record: ord-dfaf0f514424419ca3fcc65703b4df1f
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780483

Reaction notes

Loading…