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

HRID 1658578Notes

Reaction equation

HRID 1658578 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.[NH2:15][C:16]1[CH:21]=[C:20](Cl)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].CN(C)C=O>O>[NH2:15][C:16]1[CH:21]=[C:20]([S:14][C:11]2[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=2)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]

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 4.1 g. potassium carbonate, 3.7 g. p-thiocresol and 5.1 g. 2-amino-4-chloro-1-nitrobenzene in 20 ml. dimethylformamide is stirred under nitrogen for 20 hours at 20°-25°C, water is added and the product filtered off. Recrystallization from methanol gives 2-amino-4-(p-methylphenylthio)-1-nitrobenzene.

Workup

  1. additionA mixture of 4.1 g
  2. filtrationthe product filtered off
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-cc5d21d9b0a8418eb058d712bf6d875e
Source dataset
uspto-grants-1976_06
Patent number
US03965113

Reaction notes

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