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

HRID 2359932Notes

Reaction equation

HRID 2359932 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-729a3d156c8d4c799d7aa2a7114d7550
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

Loading…