3-Bromophenyl isocyanate → N-(2-hydroxy-4-nitrophenyl)-N'-(3-bromophenyl)urea

HRID 323036

Reaction equation

HRID 323036 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].[Br:12][C:13]1[CH:14]=[C:15]([N:19]=[C:20]=[O:21])[CH:16]=[CH:17][CH:18]=1>>[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:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Br:12])[CH:14]=1)=[O:21]

Participants

3

Reactant 2

HCID 1410013-Bromophenyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184715N-(2-hydroxy-4-nitrophenyl)-N'-(3-bromophenyl)ureaYield 87%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(3-bromo phenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 3-bromo 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 (0.96 g, 87%). EI-MS m/z 350 (M−H)−

Workup

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

Sources & evidence

ORD record
ord-ee8cb439a0e8475ab05b9bfca1497727
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Linked notes

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