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

HRID 567979Notes

Reaction equation

HRID 567979 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:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][CH:14]=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:16]1[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][CH:15]=1)=[O:21]

Participants

3

Reactant 2

HCID 756094-Bromophenyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184636N-(2-hydroxy-4-nitrophenyl)-N'-(4-bromophenyl)ureaYield 37%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(4-bromophenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 4-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(0.41 g, 37%). EI-MS m/z 352(M+H)+.

Workup

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

Sources & evidence

ORD record
ord-52f245df686142b596506ebeb4e98972
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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