反応 #921

反応方程式

ammonium chloride

n-butyllithium

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

N,N-dimethylcarbamyl chloride

HCl

→

title compound

収率 50.2%

3-[[-(1,1-Dimethylethyl)amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-2-carboxamide

収率 50.2%

溶媒

—

hexanes

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   温度to maintain the temperature below -65° C
3. 3
   温度to warm to room temperature
4. 4
   workup.STIRRINGstir for ca. 1.5 hours
5. 5
   温度The reaction mixture was cooled to ca. 5° C.
6. 6
   workup.STIRRINGThe reaction mixture was stirred for ca. 15 minutes
7. 7
   その他the aqueous phase was separated from the THF phase
8. 8
   抽出extracted with ethyl acetate
9. 9
   洗浄The combined THF and ethyl acetate extracts were washed with brine
10. 10
    乾燥dried (MgSO4)
11. 11
    濃縮concentrated in vacuo to an oil
12. 12
    その他The oil was chromatographed on silica with (20% ethyl acetate/80% n-butyl chloride)

実験手順

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 a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -60° C., 25 mL (61.5 mmol) 2.46M n-butyllithium in hexanes. The reaction mixture was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added dropwise a solution of 3.1 mL (33 mmol) of N,N-dimethylcarbamyl chloride in 10 mL of THF at such a rate as to maintain the temperature below -65° C. The reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to ca. 5° C. and 60 mL of 50% ammonium chloride solution was added. The reaction mixture was stirred for ca. 15 minutes. The pH was adjusted to ca. 3 with 1N HCl (ca. 30 mL), and the aqueous phase was separated from the THF phase and extracted with ethyl acetate. The combined THF and ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to an oil. The oil was chromatographed on silica with (20% ethyl acetate/80% n-butyl chloride) affording 4.33 g of the title compound as a pale yellow solid.

出典