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Potassium Carbonate → 3-(4-Methyl-2-nitro-phenylsulfanyl)-phenylamine

HRID 2197796
Notes
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Reaction equation

HRID 2197796 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([SH:26])[CH:23]=[CH:24][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:26][C:22]2[CH:21]=[C:20]([NH2:19])[CH:25]=[CH:24][CH:23]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 315773-AminothiophenolHCID 713468894-Methyl-2-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 684579173-(4-Methyl-2-nitro-phenylsulfanyl)-phenylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
10 °C

Procedure

The product from Example 4a (1.00 g, 3.51 mmol) and 3-Amino-benzenethiol (658 mg, 5.26 mmol) were dissolved in DMF to which was added K2CO3 (848 mg, 6.14 mmol). The reaction mixture was then heated to 10° C. for 16 hrs. Reaction mixture was then cooled to room temperature, diluted with water and extracted with ethyl acetate providing the title compound (650 mg, 71%).

Workup

  1. customReaction mixture
  2. temperaturewas then cooled to room temperature
  3. extractionextracted with ethyl acetate providing the title compound (650 mg, 71%)

Sources & evidence

ORD record
ord-4b5a885d69fa4038858153b37451f1f4
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