1-Isocyanato-2-(methylsulfanyl)benzene → N-(2-hydroxy-4-nitro phenyl) N'-(2-methylthio phenyl) urea

HRID 612650Notes

Reaction equation

HRID 612650 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][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]=[C:21]=[O:22]>>[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:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:13][CH3:12])=[O:22]

Participants

3

Reactant 2

HCID 27369891-Isocyanato-2-(methylsulfanyl)benzeneHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 9840030N-(2-hydroxy-4-nitro phenyl) N'-(2-methylthio phenyl) ureaYield 61%

Procedure

The urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 2-methylthio phenyl isocyanate (3.24 mmol) by general Method B. The product was purified by dilution with methylene chloride and precipitation with hexanes. Filtering afforded the title compound (0.63 g, 61%) EI-MS m/s 320(M+H)+

Workup

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

Sources & evidence

ORD record
ord-e140b2089ecf494c95c7c6b529dd7900
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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