Hydroamination Reaction Catalyzed by Acid Activated Bentonite Under Atmospheric Pressure

Author(s): Heng Zhang , Zhao-Lei Yang , Yan-Xin Li , Bin Zhao .

Journal Name: Current Organic Synthesis

Volume 10 , Issue 2 , 2013

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Abstract:

Hydrochloric acid activated bentonite was used as a catalyst for hydroamination of cyclohexene with p-toluenesulfonamide under atmospheric pressure. The structure and surface acid property of the catalyst were studied by XRD and NH3-TPD. The effects of acid treatment condition and solvent on the yield of N-cyclohexyl-p-toluenesulfonamide were specifically studied. It was found that apolar aprotic solvents were the suitable solvents for this reaction. The bentonite activated by 2 mol/L hydrochloric acid showed the highest activity and the yield of N-cyclohexyl-p-toluenesulfonamide reached 83.7% after 2 hours reflux using toluene as the solvent. The different substituted location and different substituted group on benzene ring of the anilines have important effects on the yields of products and the presence of the electron-withdrawing substituent is in favor of the reaction.

Keywords: Bentonite, hydroamination, p-toluenesulfonamide, cyclohexene, aniline

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Article Details

VOLUME: 10
ISSUE: 2
Year: 2013
Page: [333 - 336]
Pages: 4
DOI: 10.2174/1570179411310020008
Price: $58

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