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

HRID 1679448Notes

Reaction equation

HRID 1679448 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-29647a3530db458d9f243790c7eefce4
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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