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

HRID 1415528Notes

Reaction equation

HRID 1415528 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][N:13]1[CH:17]=[CH:16][N:15]=[C:14]1[SH:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[NH2:1][C:2]1[CH:7]=[C:6]([S:18][C:14]2[N:13]([CH3:12])[CH:17]=[CH:16][N:15]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 178480602HCID 178480602, compound

Product 1

HCID 214827895-[(1-Methyl-1H-imidazol-2-yl)sulfanyl]-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.5 G. of 2-amino-4-chloro-1-nitrobenzene, 3.4 g. of 1-methyl-2-mercapto-imidazole and 4.2 g. potassium carbonate in 20 ml. dimethylformamide is heated overnight at 110°-120° C., then cooled, and poured into water. The product is filtered off and recrystallized from aqueous methanol to give 2-amino-4-(1-methylimidazol-2-ylthio)-1-nitrobenzene.

Workup

  1. additionA mixture of 2.5 G
  2. temperaturecooled
  3. filtrationThe product is filtered off
  4. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-d4ddb38805a4419b8a7d277fc73d09d9
Source dataset
uspto-grants-1977_01
Patent number
US04005202

Reaction notes

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