Hydrochloric Acid → 3-Acetyl-1-(phenylsulfonyl)pyrrole

HRID 248488Notes

Reaction equation

HRID 248488 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(=[O:17])[CH3:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)C>[C:15]([C:13]1[CH:12]=[CH:11][N:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])[CH:14]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 1401461-PhenylsulfonylpyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5557923-Acetyl-1-(phenylsulfonyl)pyrrole

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

A mixture of 41.4 g of 1-(phenylsulfonyl-1H-pyrrole, prepared as described above, and 17.16 g of acetyl chloride in 200 ml of dichloroethane was added to a suspension of 32 g of aluminum chloride in 200 ml of dichloroethane. The reaction was stirred for one hour, poured onto a mixture of ice and concentrated hydrochloric acid and extracted several times with ether. The extracts were combined and evaporated. The residue was triturated with ether and the solid collected, giving 39 g of 3-acetyl-1-(phenylsulfonyl)-1H-pyrrole.

Workup

  1. customprepared
  2. extractionextracted several times with ether
  3. customevaporated
  4. customThe residue was triturated with ether
  5. customthe solid collected

Sources & evidence

ORD record
ord-da53db854dce4327b7f5667950785d46
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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