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

HRID 567964Notes

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′-phenylurea 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-7a65870d21b449d3a2c5134c81b32942
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180675B2

Reaction notes

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