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

HRID 612636Notes

Reaction equation

HRID 612636 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-methoxy phenyl isocyanate (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-10b2416ca5fd4b2c8be6fd83a277ebef
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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