Dimethylformamide → 5-[(4-Methylphenyl)sulfanyl]-2-nitroaniline

HRID 1414768Notes

Reaction equation

HRID 1414768 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][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[NH2:1][C:2]1[CH:7]=[C:6]([S:19][C:16]2[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78114-MethylbenzenethiolHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 203628195-[(4-Methylphenyl)sulfanyl]-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.5 g. 2-amino-4-chloro-1-nitrobenzene, 3.6 g. p-thiocresol, 4.2 g. potassium carbonate in 20 ml. dimethylformamide is stirred overnight at room temperature, then poured into water. The crude product, recrystallized from methanol, gives 2-amino-4-(p-methylphenylthio)-1-nitrobenzene.

Workup

  1. additionA mixture of 2.5 g
  2. customThe crude product, recrystallized from methanol

Sources & evidence

ORD record
ord-476f98abd7b544b7b4a2279f3a660654
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

Loading…