Dimethylformamide → 5-[(1H-Imidazol-2-yl)sulfanyl]-2-nitroaniline

HRID 1580965Notes

Reaction equation

HRID 1580965 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.CN(C)C=O.[H-].[Na+].[NH2:14][C:15]1[CH:20]=[C:19](Cl)[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]>O>[NH2:14][C:15]1[CH:20]=[C:19]([S:1][C:2]2[NH:3][CH:4]=[CH:5][N:6]=2)[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 742185-Chloro-2-nitroanilineHCID 178527877HCID 178527877, compound

Product 1

HCID 214827775-[(1H-Imidazol-2-yl)sulfanyl]-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.0 g. 2-mercaptoimidazole in 25 ml. dimethylformamide is treated with 0.85 g. of 57% sodium hydride (in oil suspension). 3.0 G. of 2-amino-4-chloro-1-nitrobenzene is added and the mixture heated overnight at 150°-155°C. The mixture is diluted with water, filtered and the crude product washed with chloroform, recrystallized from aqueous methanol to yield 2-amino-4-(imidazol-2-ylthio)-1-nitrobenzene.

Workup

  1. temperaturethe mixture heated overnight at 150°-155°C
  2. filtrationfiltered
  3. washthe crude product washed with chloroform
  4. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-eda2d5b553c94f6ba65e142e86aef5ac
Source dataset
uspto-grants-1976_01
Patent number
US03935209

Reaction notes

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