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

HRID 567978Notes

Reaction equation

HRID 567978 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-bromophenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 3-bromophenylisocyanate (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(0.96g, 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-672b512ae06f436884ec7f725649795c
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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