2-Fluorophenyl isocyanate → N-(2-Fluorophenyl)-N′-(2-hydroxy-4-nitrophenyl)urea

HRID 1385355Notes

Reaction equation

HRID 1385355 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]=[CH:15][C:14]=1[N:19]=[C:20]=[O:21]>>[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:20]([NH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[F:12])=[O:21]

Participants

3

Reactant 2

HCID 855882-Fluorophenyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184605N-(2-Fluorophenyl)-N′-(2-hydroxy-4-nitrophenyl)ureaYield 62.5%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(2-fluorophenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 2-fluoro 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 (0.59 g, 31%). EI-MS m/z 292 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-7a70f79cc8434715a52e0c9e80d8b917
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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