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

HRID 1419366Notes

Reaction equation

HRID 1419366 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-b08ee1a4d44f482dba1b3cd069631fe0
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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