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

HRID 2197957
Notes
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Reaction equation

HRID 2197957 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

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-82e0ea37af804560abe394a97d72b584
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08338605B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes