高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (1): 56.

• 研究论文 • 上一篇    下一篇

N-2-氯苄基苯甲酰胺的固相合成及其晶体结构分析

罗君涛, 黄文强   

  1. 南开大学吸附分离功能高分子材料国家重点实验室, 高分子化学研究所, 天津 300071
  • 收稿日期:2002-12-27 出版日期:2004-01-24 发布日期:2004-01-24
  • 通讯作者: 黄文强(1940年出生),男,硕士,教授,博士生导师,主要从事功能高分子、组合化学和固相有机合成研究.E-mail:hwq60@nanka.iedu.cn E-mail:hwq60@nanka.iedu.cn
  • 基金资助:

    国家自然科学基金(批准号:20074017)资助

Solid Phase Synthesis of N-2-Chlorobenzylbenzamide and Its Crystal Structure

LUO Jun-Tao, HUANG Wen-Qiang   

  1. State Key Laboratory of Functional Polymer Materials for Adsorption and Separation, Institute of Polymer Chemistry, Nankai University, Tianjin 300071, China
  • Received:2002-12-27 Online:2004-01-24 Published:2004-01-24

摘要: N-2-氯苄基苯甲酰胺采用固相法制备.聚苯乙烯磺酰氯(1)在吡啶存在下与2-氯苄胺反应得到N-2-氯苄基磺酰胺树脂(2),进一步在吡啶催化下用苯甲酰氯进行酰化得到N-2-氯苄基-N-苯甲酰基磺酰胺树脂(3).用TiCl4/Zn/THF试剂处理,从树脂3上解脱得到产物N-2-氯苄基苯甲酰胺(4),产率92%.N-2-氯苄基苯甲酰胺的晶体属于单斜晶系,P21空间群,晶胞参数:a=0.7149(3)nm,b=0.8772(4)nm,c=0.9704(4)nm;β=95.172(7)°;晶体结构中存在两种分子间氢键相互作用.

关键词: 固相有机合成, N-2-氯苄基苯甲酰胺, 晶体结构

Abstract: The title compound was prepared by solid phase synthesis technique. Polystyryl sulfonyl chloride resin 1 was treated with 2-chlorobenzylamine in the presence of pyridine to yield polymer-supported N-2-chlorobenzyl sulfonamide 2. Resin 2 was acylated with benzoyl chloride catalyzed by pyridine to give N-2-chlorobenzyl-N-benzoyl sulfonamide resin 3. After the cleavage of resin 3 using TiCl4/Zn/THF in a radical way, N-2-chlorobenzylbenzamide(4) was obtained in 92% overall yield. The crystal structure of N-2-chlorobenzylbenzamide was reported as follows: N-2-chlorobenzylbenzamide crystallizes in the monoclinic space group P21 with cell parameters: a=0.714 9(3)nm, b=0.877 2(4)nm, c=0.970 4(4)nm; β=95.172(7)°. N-2-Chlorobenzylbenzamide has two kinds of intermolecular hydrogen bonds in the crystal.

Key words: Solid phase organic synthesis, N-2-Chlorobenzylbenzamide, Crystal structure

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