Thiophenol → Methyl 4-methyl-1-phenyl-5-(phenylthio)-1H-pyrrole-3-carboxylate

HRID 1670859Notes

Reaction equation

HRID 1670859 reaction equation
[CH3:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.IN1C(=O)CCC1=O.[C:25]1([SH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:6]=1[S:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 57687732Methyl 4-methyl-1-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 57687725Methyl 4-methyl-1-phenyl-5-(phenylthio)-1H-pyrrole-3-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-methyl-1-phenyl-1H-pyrrole-3-carboxylate (540 mg) in tetrahydrofuran (10 mL) were added N-iodosuccinimide (677 mg) and thiophenol (0.257 mL), and the mixture was stirred at room temperature for 2 days. Saturated aqueous sodium thiosulfate solution (10 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a pale-yellow oil (yield 812 mg, about 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab26a4131b6b4dec880f49c9410c8535
Source dataset
uspto-grants-2011_08
Patent number
US07994205B2

Reaction notes

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