Trifluoromethanesulfonic acid → Methyl 5-(p-chlorophenyl)-4-[(trifluoromethyl)thio]pyrrole-2-carboxylate

HRID 1975205Notes

Reaction equation

HRID 1975205 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3](O)(=O)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.FC(F)(F)SCl>C(Cl)Cl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:17]=2[S:3][C:2]([F:8])([F:7])[F:1])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 67900Methanesulfenyl chloride, trifluoro-HCID 18930419Methyl 5-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 18930391Methyl 5-(p-chlorophenyl)-4-[(trifluoromethyl)thio]pyrrole-2-carboxylateYield 902.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

Trifluoromethanesulfonic acid (0.27 g, 0.001795 mol) is added to a solution of methyl 5-(p-chlorophenyl)pyrrole-2-carboxylate (4.23 g, 0.01795 mol) in methylene chloride (70 mL) at -30° C. This mixture is treated with trifluoromethylsulfenyl chloride (4.0 g, 0.0293 mol), stirred for 30 minutes at -15° C., warmed to room temperature with stirring for three hours, diluted with methylene chloride, washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title product as an off-white solid (5.44 g, mp 133°-137° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. temperaturewarmed to room temperature
  2. stirringwith stirring for three hours
  3. washwashed with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c5616f2b49747e4bfe6fa31fd766ba0
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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