4-Chloro-3-nitrotoluene → 3-(4-Methyl-2-nitro-phenylsulfanyl)-phenylamine

HRID 2358792Notes

Reaction equation

HRID 2358792 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([S:8][C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=2)=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

6

Reactant 3

HCID 69764-Chloro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 315773-Aminothiophenol

Product 1

HCID 684579173-(4-Methyl-2-nitro-phenylsulfanyl)-phenylamineYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was prepared from 3-Amino-benzenethiol (5.034 g, 40.21 mmol), 1-Chloro-4-methyl-2-nitro-benzene (4.600 g, 26.81 mmol) and K2CO3 (6.484 g, 46.92 mmol) dissolved in DMF and heated to 100° C. for 16 hrs. At this time the reaction mixture was cooled to room temperature and diluted with water, extracted with ethyl acetate. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (2.3 g, 32%).

Workup

  1. temperatureAt this time the reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b91a483f8ffe47f5814ccaa06445b4e6
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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