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

HRID 1415531Notes

Reaction equation

HRID 1415531 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 155°-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 155°-155° C
  2. filtrationfiltered
  3. washthe crude product washed with chloroform
  4. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-6a7ca018e68e44ddb67d3ee8d685cda7
Source dataset
uspto-grants-1977_01
Patent number
US04005202

Reaction notes

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