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

HRID 1385354Notes

Reaction equation

HRID 1385354 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].[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23])([O-:14])=[O:13]>>[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:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N+:12]([O-:14])=[O:13])=[O:23]

Participants

3

Reactant 2

HCID 768342-Nitrophenyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184705N-(2-hydroxy-4-nitrophenyl)-N'-(2-nitrophenyl)ureaYield 44%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(2-nitro phenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 2-nitro 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 (0.44 g, 44%). EI-MS m/z 319 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-37b4fdfb74864022ab1e4542079374ec
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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