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

HRID 612644Notes

Reaction equation

HRID 612644 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-14534b3035154c15b748c59fa68f54b7
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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