3-Methoxyphenyl isocyanate → N-(2-Hydroxy-4-nitrophenyl)-N'-(3-methoxyphenyl)urea

HRID 567973Notes

Reaction equation

HRID 567973 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].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([N:20]=[C:21]=[O:22])[CH:17]=[CH:18][CH:19]=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:21]([NH:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[CH:15]=1)=[O:22]

Participants

3

Reactant 2

HCID 878433-Methoxyphenyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 21184674N-(2-Hydroxy-4-nitrophenyl)-N'-(3-methoxyphenyl)ureaYield 46.2%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(3-methoxyphenyl)urea was prepared from 2-hydroxy 4-nitro aniline (154 mg, 1.0 mmol) and 3-methoxyphenylisocyanate(1.0 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 (140 mg, 46%). EI-MS m/z 302(M−H)−.

Workup

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

Sources & evidence

ORD record
ord-03267988ad484a20a809e2ef1df51f6c
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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