Hydrochloric Acid → 3-(p-Chlorophenyl)-2-[(trifluoromethyl)thio]pyrrole

HRID 129637Notes

Reaction equation

HRID 129637 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](C(OCC)=O)=[CH:10][NH:11][C:12]=2[S:13][C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.Cl>[OH-].[Na+].C(CN)O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][NH:11][C:12]=2[S:13][C:14]([F:16])([F:15])[F:17])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 18930389Ethyl 4-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carboxylate

Product 1

HCID 189304043-(p-Chlorophenyl)-2-[(trifluoromethyl)thio]pyrroleYield 75.2%

Reagents, catalysts & solvents 3

HCID 700EthanolamineSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 4-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carboxylate (8.0 g, 0.023 mol) in 10% aqeuous sodium hydroxide solution is refluxed for several hours, stirred at room temperature overnight, poured into ice-water, treated with concentrated hydrochloric acid and extracted with ether. The combined organic extracts are washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a brown semi-solid. A solution of the semi-solid (6.9 g) in ethanolamine is heated at 110° C. for several hours, poured into ice-water and extracted with chloroform. The combined organic extracts are washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a brown oil. The oil is dissolved in methylene chloride, filtered through a bed of silica gel and the filtrate is concentrated in vacuo to obtain the title product as a grey semi-solid (4.8 g, mp 44°-46° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts are washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a brown semi-solid
  6. extractionextracted with chloroform
  7. washThe combined organic extracts are washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto give a brown oil
  11. filtrationfiltered through a bed of silica gel
  12. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-268e20b7266c4ef184704095c9e2689f
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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