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Citation: HU Yi, KANG Hui, LI Heng, WEI Ping. N-Alkylation Reaction of N-Monosubstituted Sulfonamides Promoted by Potassium Fluoride in Ionic Liquids[J]. Chinese Journal of Applied Chemistry, ;2007, 24(4): 474-476. shu

N-Alkylation Reaction of N-Monosubstituted Sulfonamides Promoted by Potassium Fluoride in Ionic Liquids

1.
College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009

Corresponding author: HU Yi,
Received Date: 20 July 2006
Available Online: 13 September 2006

The N-alkylation of N-monosubstituted sulfonamides with alkyl halides promoted by KF using ionic liquids as reaction media was reported in this paper. Four different ionic liquids,[Bmim]BF₄,[Bpy]BF₄ and [Bpy]PF₆ were investigated,and [Bmim]PF₆ showed the best effect when used as the reaction media,giving the highest yield in the shortest reaction time.Promoted by KF in [Bmim]PF₆,N-aryl or N-alkyl monosubstituted sulfonamides could react with various activated halides and unactivated primary halides smoothly.Reactions were performed at 85℃ for 2~10 hours,and thirteen N-alkylation products were obtained with 70%~97% yields.Moreover,the ionic liquid recovered could be reused for three times with no appreciable decrease in yield and reaction rate.As demonstrated in this paper,both KF,which was used as mild base,and the ionic liquid [Bmim]PF₆ promoted the alkylation reaction efficiently.
- ionic liquid,
- sulfonamide,
- alkyl halide,
- alkylation,
- potassium fluoride
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