2-(Trifluoromethoxy)phenyl Isocyanate → N-(2-Hydroxy-4-nitrophenyl)-N'-(2-trifluoromethyloxyphenyl)urea

HRID 1385358Notes

Reaction equation

HRID 1385358 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23]>>[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][C:13]([F:12])([F:24])[F:25])=[O:23]

Participants

3

Reactant 2

HCID 6089532-(Trifluoromethoxy)phenyl IsocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184649N-(2-Hydroxy-4-nitrophenyl)-N'-(2-trifluoromethyloxyphenyl)ureaYield 60%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(2-trifluoromethyloxyphenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 2-trifluoromethoxy phenyl isocyanate (3.24 mmol) according to the procedure in General Method B. The product was purified by dilution with methylene chloride and precipitation with hexanes. Filtering afforded the title compound (0.69 g, 60%). EI-MS m/z 358 (M+H)+

Workup

  1. customThe product was purified by dilution with methylene chloride and precipitation with hexanes
  2. filtrationFiltering

Sources & evidence

ORD record
ord-d2b037c2cccb4e5fbcd91efb6ba7d9cd
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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