Reaction #908

Reaction equation

N-(1,1-dimethylethyl)-1H-pyrrole-3 -sulfonamide

methyl iodide

potassium t-butoxide

→

N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

Solvents

N,N-dimethylforamide

ethyl acetate

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   Washwashed three times with 1N HCl
3. 3
   Dryingonce with brine, dried (MgSO4)
4. 4
   Otherevaporated to an oily solid which
5. 5
   Otherwas triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C.

Procedure

A solution of N-(1,1-dimethylethyl)-1H-pyrrole-3 -sulfonamide 9 g (0.044 mol) in 90 mL N,N-dimethylforamide was cooled to 15° C. under a nitrogen atmosphere. To this was added 3.2 mL (0.053 mol) of methyl iodide followed by 5.43 g (0.048 mol) of potassium t-butoxide. The mixture was warmed at ca. 60° C. for 2 hours then allowed to cool to room temperature and stirred for ca. 2 hours. The reaction mixture was diluted with ethyl acetate, washed three times with 1N HCl, once with brine, dried (MgSO4) and evaporated to an oily solid which was triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C.

Source