化工进展 ›› 2017, Vol. 36 ›› Issue (S1): 402-405.DOI: 10.16085/j.issn.1000-6613.2017-0085

• 精细化工 • 上一篇    下一篇

5-苯基-7-氯-1,3-二氢-2H-1,4-苯并二氮杂(艹卓)-2-酮的微波合成

吴双双, 陆勇, 王文峰, 胡燕飞, 陈天云   

  1. 合肥工业大学化学与化工学院, 安徽 合肥 230009
  • 收稿日期:2017-01-16 修回日期:2017-04-01 出版日期:2017-12-31 发布日期:2017-12-13
  • 通讯作者: 陈天云,教授,博士生导师,主要从事有机化学品合成与工程化研究。
  • 作者简介:吴双双(1991-),男,硕士研究生,从事精细有机合成技术研究。

Synthesis of 5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one under microwave irradiation

WU Shuangshuang, LU Yong, WANG Wenfeng, HU Yanfei, CHEN Tianyun   

  1. School of Chemistry and Chemical Engineering, Hefei University Technology, Hefei 230009, Anhui, China
  • Received:2017-01-16 Revised:2017-04-01 Online:2017-12-31 Published:2017-12-13

摘要: 以2-氨基-5氯-二苯甲酮和氯乙酰氯为原料通过氯乙酰化合成2-氯乙酰氨基-5-氯-二苯甲酮,再与乌洛托品在微波辐射下发生德尔宾反应和酮胺缩合反应环合得到5-苯基-7-氯-1,3-二氢-2H-1,4-苯并二氮杂(艹卓)-2-酮。通过单因素实验方法研究了主要反应条件对产品收率的影响,确定了环合的最佳反应条件为:反应温度100℃,n(2-氯乙酰氨基-5-氯-二苯甲酮)∶n(乌洛托品)=1∶2.0,反应时间50min,36%乙酸2mL,无水乙醇25mL,最佳反应条件下,环合反应收率可达到89.6%,反应总收率为84.8%,实验重现性较好。利用熔点测定、红外光谱分析和核磁共振氢谱分析,对产品进行了物性和结构表征,表明合成物质确为目标产物。

关键词: 5-苯基-7-氯-1, 3-二氢-2H-1, 4-苯并二氮杂(艹卓)-2-酮, 2-氨基-5氯-二苯甲酮, 微波辐射, 酰化, 环合

Abstract: In this paper,2-amino-5-chloro-benzophenone and chloroacetyl chloride were used as starting materials to synthesize 2-chloroacetylamino-5-chloro-benzophenone by chloroacetylation and then reacted with hexamethylenetetramine under microwave irradiation by Delépine reaction and the ketamine condensation reaction to give 5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one. The influence of the main reaction conditions on the yield of the product was studied by single factor experiment. The optimum reaction conditions were determined as follows:reaction temperature 100℃, n(2-chloroacetylamino-5-chloro-benzophenone):n(hexamethylenetetramine)=1:2.0, reaction time 50min, 2mL of 36% acetic acid,25mL of anhydrous ethanol and the yield of the cyclization reaction reached 89.6% under the optimal reaction conditions, the total yield was 84.8%, The experimental reproducibility is better. The products were characterized by melting point, IR and 1HNMR. The results showed that the synthesized product was the target product.

Key words: 5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepine-2-one, 2-amino-5-chloro-benzophenone, microwave irradiation, chloroacetylation, cyclization

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