Reaction #913

Reaction equation

N-(1,1-dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide

trifluoroacetic acid

→

title compound

Yield 79.6%

1-Methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide

Yield 79.6%

Solvents

methylene chloride

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated to a tan solid
2. 2
   workup.ADDITIONDiethyl ether was added to the tan solid
3. 3
   Otherwas removed by evaporation
4. 4
   Otherto remove residual TFA
5. 5
   Filtrationfiltered

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.

Source