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

HRID 612641Notes

Reaction equation

HRID 612641 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-bromo phenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 4-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 (0.41 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-2e89c0443db64907b9f2cf69bd3e2554
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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