Reaktion #912

Reaktionsgleichung

HCl

n-butyllithium

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

dimethyldisulfide

→

title compound

Ausbeute 58.8%

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

Ausbeute 58.8%

Lösungsmittel

—

hexanes

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle