2,6-Difluorophenyl isocyanate → N-(2-Hydroxy4-nitrophenyl)-N'-(2,6-difluorophenyl)urea

HRID 567984Notes

Reaction equation

HRID 567984 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]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[N:20]=[C:21]=[O:22]>>[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:21]([NH:20][C:14]1[C:15]([F:19])=[CH:16][CH:17]=[CH:18][C:13]=1[F:12])=[O:22]

Participants

3

Reactant 2

HCID 5221622,6-Difluorophenyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184787N-(2-Hydroxy4-nitrophenyl)-N'-(2,6-difluorophenyl)ureaYield 91%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(2,6-difluorophenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 2,6-difluorophenylisocyanate(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(0.91 g, 91%). EI-MS m/z 308(M−H)−.

Workup

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

Sources & evidence

ORD record
ord-93889d42d90f478791c656267150cf51
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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