Trifluoroacetic acid → 1-Methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide

HRID 2259181

Reaction equation

HRID 2259181 reaction equation
CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[S:15][CH3:16])(=[O:8])=[O:7])(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:14][N:11]1[CH:12]=[CH:13][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[C:10]1[S:15][CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19693814N-(1,1-Dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide

Product 1

HCID 196938491-Methyl-2-(methylthio)-1H-pyrrole-3-sulfonamideYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.63 g (17.66 mmol) N-(1,1-dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide in 50 mL of methylene chloride was added 50 mL of trifluoroacetic acid (TFA) under a nitrogen atmosphere. The orange reaction mixture was stirred at room temperature overnight ca. 16 hours. The reaction mixture was concentrated to a tan solid. Diethyl ether was added to the tan solid and was removed by evaporation to remove residual TFA. The solid was suspended in diethyl ether and filtered giving 2.9 g of the title compound as a solid, m.p. 135°-137° C. 1H NMR (Acetone-d6, 200 MHz.) δ: 6.93(d,1H), 6.45(d,1H), 6.19(bs,2H), 3.78(s,3H), 2.33(s,3H).

Workup

  1. concentrationThe reaction mixture was concentrated to a tan solid
  2. additionDiethyl ether was added to the tan solid
  3. customwas removed by evaporation
  4. customto remove residual TFA
  5. filtrationfiltered

Sources & evidence

ORD record
ord-fa9c6b4d14d04f43b75d05948c71d030
Source dataset
uspto-grants-1995_12
Patent number
US05472933

Linked notes

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