Reacción #912

Ecuación de reacción

HCl

n-butyllithium

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

dimethyldisulfide

→

title compound

Rendimiento 58.8%

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

Rendimiento 58.8%

Disolventes

—

hexanes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise at such a rate as
2. 2
   Otrothe temperature below -65° C
3. 3
   Otrothe resulting reaction mixture
4. 4
   Temperaturato warm to room temperature
5. 5
   workup.STIRRINGstir for ca. 1.5 hours
6. 6
   TemperaturaThe reaction mixture was cooled to 0° C.
7. 7
   OtroThe THF phase was separated
8. 8
   Lavadowashed with brine
9. 9
   Secadodried (MgSO4)
10. 10
    Concentraciónconcentrated in vacuo
11. 11
    OtroThe crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes)

Procedimiento

To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78° C. was added dropwise at such a rate as to keep the temperature below -65° C. 25.52 mL (61.5 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added 2.97 mL (33 mmol) of dimethyldisulfide in one portion and the resulting reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to 0° C. and acidified with 1N HCl. The THF phase was separated washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes) affording 4.63 g of the title compound as an off white solid, m.p. 116°-119° C.

Fuente