1-tosyl-3-acetylpyrrole → 2-Chloro-1-[1-(4-methylbenzene-1-sulfonyl)-1H-pyrrol-3-yl]ethan-1-one

HRID 345951Notes

Reaction equation

HRID 345951 reaction equation
[Cl-].[Ca+2].[Cl-].[C:4]([C:7]1[CH:11]=[CH:10][N:9]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:8]=1)(=[O:6])[CH3:5].[Cl:22]C(=C(Cl)C(Cl)=C(Cl)C(Cl)Cl)C=O>CO>[Cl:22][CH2:5][C:4]([C:7]1[CH:11]=[CH:10][N:9]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 27377871-tosyl-3-acetylpyrroleHCID 5284359Calcium ChlorideHCID 54378597HCID 54378597, compound

Product 1

HCID 151807422-Chloro-1-[1-(4-methylbenzene-1-sulfonyl)-1H-pyrrol-3-yl]ethan-1-oneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 cm3 one neck flask fitted with a condenser and a calcium chloride guard, 4 g of 3-acetyl-1-tosyl pyrrole 2 (15 mmoles) was introduced together with 30 cm3 of methanol. Then 4.5 g of 2,3,4,5,6,6-hexachloro-2,4-hexadiene-1-one (15 mmoles) was set under reflux during 6 hours and maintained under stirring at ambient temperature during one night. The solvent was evaporated and the crude product (8.5 g) was dissolved in 15 cm3 of chloroform, filtered (the pentachlorophenol was not very soluble in this solvent) and separated on silica gel column (250 g; 60-200 82 m; eluting with 1-29-70 acetic acid-ethyl acetate-heptane; VR =650 cm3) to give 2.35 g of white crystals 3 (M=297.5, yield: 53%).

Workup

  1. temperatureunder reflux during 6 hours
  2. temperaturemaintained
  3. customThe solvent was evaporated
  4. dissolutionthe crude product (8.5 g) was dissolved in 15 cm3 of chloroform
  5. filtrationfiltered (the pentachlorophenol
  6. customseparated on silica gel column (250 g; 60-200 82 m; eluting with 1-29-70 acetic acid-ethyl acetate-heptane; VR =650 cm3)

Sources & evidence

ORD record
ord-8857202108304af09e4bcc89786b322e
Source dataset
uspto-grants-1991_10
Patent number
US05059694

Reaction notes

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