تفاعل #912

معادلة التفاعل

HCl

n-butyllithium

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

dimethyldisulfide

→

title compound

المردود 58.8%

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

المردود 58.8%

المذيبات

—

hexanes

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر