1,2-Dichloroethane → 2-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]-5-[(trifluoromethyl)thio]pyrrole

HRID 375197Notes

Reaction equation

HRID 375197 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:4][CH:3]=1.[F:20][C:21]([F:25])([F:24])[S:22]Cl.FC(F)(F)S(O)(=O)=O.ClCCCl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([S:22][C:21]([F:25])([F:24])[F:20])=[CH:11][C:12]=2[S:13]([C:16]([F:17])([F:19])[F:18])(=[O:14])=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 62406Trifluoromethanesulfonic acidHCID 67900Methanesulfenyl chloride, trifluoro-HCID 10448068HCID 10448068, compound

Product 1

HCID 189304062-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]-5-[(trifluoromethyl)thio]pyrroleYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole (2.47 g, 0.0080 mol), trifluoromethylsulfenyl chloride (2,18 g, 0,016 mol), trifluoromethanesulfonic acid (0.12 g, 0.0008 mol) and 1,2-dichloroethane (15 mL) is placed in a pressure tube, heated at 70° C. for five days, diluted with methylene chloride, washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an amber syrup. Flash chromatography of the syrup using silica gel and a 1:5 ethyl acetate/hexanes solution gives the title product as an off-white solid (2.36 g, mp 118°-122° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain an amber syrup

Sources & evidence

ORD record
ord-cd70436d7e204aa8b478d42e824b15a3
Source dataset
uspto-grants-1996_01
Patent number
US05484807

Reaction notes

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