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

HRID 567982Notes

Reaction equation

HRID 567982 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-nitrophenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 2-nitrophenylisocyanate (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-e490e06144694cba960729fa4f462bf7
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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