Réaction #912

Équation de réaction

HCl

n-butyllithium

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

dimethyldisulfide

→

title compound

Rendement 58.8%

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

Rendement 58.8%

Solvants

—

hexanes

THF

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source