Alkylamination of Aromatic Sulfonates

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Bibliographic Information

Other Title
  • 芳香族スルホン酸塩のアルキルアミノ化反応

Description

The reaction of aromatic sulfonates (sodium benzene-, toluene- and naphthalenesulfonates) with sodium amide in monoalkylamines (R=Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, and cycloHexyl) has been studied. By the reaction of aromatic sulfonates with three-fold moles of sodium amide in excess monoalkylamines at 140-170°C, alkylarylamines and aromatic primary amines were obtained in the ratios of 8: 2-9: 1. The yields of alkylarylamines were about 60-90%. Dialkylamines were alsobtained by use of excess amounts of sodium amide at high temperatures. The effects of temperature, amounts of sodium amide and monoalkylamines, and kinds of alkyl groups in monoalkylamines were examined. This reaction seems to proceed as shown in equations ( 1 ) ( 4 ). Alkylarylamines were prepared with high selectivity and in good yields by means of two-step method which consists of ( 1 ) sodation of monoalkylamines at low temperatures below 110°C and ( 2 ) alkylamination of aromatic sulfonates at high temperatures between 140°C and 160°C.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1974 (9), 1704-1707, 1974-09-10

    The Chemical Society of Japan

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