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

HRID 1956639Notes

Reaction equation

HRID 1956639 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-nitophenyl)-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-693cdcec2e0243bc97eecb046e0a7b89
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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