Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (19): 2281-2286. Previous Articles     Next Articles

Full Papers

2-氨基-4-噻唑啉酮的高效合成和晶体结构

孟祥武1,陆丰平1,2,赵华绒*,1   

  1. (1浙江大学化学系 杭州 310027)
    (2上海艾力斯医药有限公司 上海 201204)
  • 投稿日期:2011-02-16 修回日期:2011-05-16 发布日期:2011-06-07
  • 通讯作者: 赵华绒 E-mail:zhr0103@sohu.com
  • 基金资助:

    浙江省自然科学基金

Efficient Synthesis and Crystal Structure of 2-Amino-4-thiazolinones

Meng Xiangwu1 Lu Fengping1,2 Zhao Huarong*,1   

  1. (1 Department of Chemistry, Zhejiang University, Hangzhou 310027)
    (2 Allist Pharmaceuticals, Inc., Shanghai 201204)
  • Received:2011-02-16 Revised:2011-05-16 Published:2011-06-07
  • Contact: ZHAO Hua-Rong E-mail:zhr0103@sohu.com

In this paper, a simple, environment-friendly and efficient one-pot way to synthesize 2-amino-4-thiazolinones at room temperature was reported. Ethyl 2-thiocyanatoacetate was formed by substitution reaction of ethyl chloroacetate with thiocyanate in [Bmim]SCN. After that, when HOAc was employed as a catalyst, 2-amino-4-thiazolinones were produced in high yields through the nucleophilic attack of amines to ethyl 2-thiocyanatoacetate following ring-closing reaction of intermediate product S-alkyl isothioureas. As a task-specific ionic liquid, [Bmim]SCN plays a role of a solvent as well as a reactant. And it can be recycled. The crystal structure of 2-(4-ethylpiperzin-1-yl)-4-thiazolinone (3i) was confirmed by X-ray diffraction study.

Key words: thiazolinones, synthesis, task-specific ionic liquid, crystal structure