2-Thiophenesulfonyl chloride → HCID 59576359, compound

HRID 2069514Notes

Reaction equation

HRID 2069514 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][O:15][C:16]([C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1)=[O:17]>ClCCl>[CH3:14][O:15][C:16]([C:18]1[NH:19][CH:20]=[C:21]([S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:7])[CH:22]=1)=[O:17]

Participants

5

Reactant 3

HCID 855182-Thiophenesulfonyl chlorideHCID 136930Methyl pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59576359HCID 59576359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of thiophene-2-sulfonyl chloride in dichloromethane was added aluminum chloride at 0-5° C., 1H-pyrrole-2-carboxylic acid methyl ester in dichloromethane was added slowly. Reaction mixture was stirred from room temperature to 60° C. for 24 hrs. On completion of reaction; reaction mixture was poured over crushed ice and extracted with dichloromethane, organic layer was washed with 1 N NaOH solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 4-(thiophene-2-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (D1-I).

Workup

  1. customReaction mixture
  2. customOn completion of reaction
  3. customreaction mixture
  4. additionwas poured
  5. customover crushed ice
  6. extractionextracted with dichloromethane, organic layer
  7. washwas washed with 1 N NaOH solution and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d98cdce93ded45bfb47449b6df55ed2a
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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