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

HRID 323040Notes

Reaction equation

HRID 323040 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-5ec5d8f62116492996575533362e2a3b
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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