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

HRID 612645Notes

Reaction equation

HRID 612645 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-8e4cc4d2f56d497a9ffbeeae9a19fedc
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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