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2012 , Vol. 32 >Issue 01: 145 - 148

DOI: https://doi.org/10.6023/cjoc1108121

研究简报

稳定同位素标记15N-N,N-二甲基苯胺的合成

  • 杨维成 ,
  • 齐庆瑞 ,
  • 刘卫霞 ,
  • 李美华 ,
  • 罗勇
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  • a 上海化工研究院技术开发中心 上海 200062;
    b 新疆教育学院职业教育分院 乌鲁木齐 830046

收稿日期: 2011-08-12

  修回日期: 2011-09-15

  网络出版日期: 2011-09-30

基金资助

科技部转制院所专项(No. 2011EG116066)和质检总局科技专项(No. 2009IK134)资助项目.

收起

Synthesis of Isotope-Labeled 15N-N,N-Dimethylaniline

  • YANG Wei-Cheng ,
  • QI Qing-Rui ,
  • LIU Wei-Xia ,
  • LI Mei-Hua ,
  • LUO Yong
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  • a Research & Development Center, Shanghai Research Institute of Chemical Industry, Shanghai 200062;
    b Branch of Professional Education, Xinjiang Normal University, Urumqi 830046

Received date: 2011-08-12

  Revised date: 2011-09-15

  Online published: 2011-09-30

Supported by

Project supported by the Special Funds for System-Transformed Institutes of Science and Technology Ministry (No. 2011EG116066) and the Special Funds of the General Administration of Quality Supervision, Inspection and Quarantine (No. 2009IK134).

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摘要

以15NH4Cl 为同位素标记前体, 经与苯甲酰氯胺化、霍夫曼降解得到15N 标记苯胺, 15N 标记苯胺再与对甲苯磺酸酯进行甲基化反应, 合成得到一种重要的同位素标记基础试剂15N-N,N-二甲基苯胺. 以消耗的15NH4Cl 计, 三步反应总收率大于58.3%. 产品结构经红外(IR)、核磁(NMR)、高效液相(HPLC)、质谱(MS)等表征进行确定, 其化学纯度大于99.0%, 同位素丰度大于98.4% 15N.

关键词： 同位素标记; 合成; N,N-二甲基苯胺; 表征; 甲基化

本文引用格式

杨维成 , 齐庆瑞 , 刘卫霞 , 李美华 , 罗勇 . 稳定同位素标记15N-N,N-二甲基苯胺的合成[J]. 有机化学, 2012 , 32(01) : 145 -148 . DOI: 10.6023/cjoc1108121

Abstract

An efficient synthesis of 15N-N,N-dimethylaniline with 15NH4Cl as the common substrate is reported. Ammoniation of benzoyl chloride with 15NH4Cl provided 15N-benzamide, which was converted to 15N-aniline by Hofmann degradation. Methylation of 15N-aniline with methyl p-toluenesulfonate provided 15N-N,N-dimethylaniline. The overall yield of 15N-N,N-dimethylaniline in three steps was 58.3% based on 15NH4Cl consumed. As-synthesized product was shown by IR, NMR, HPLC and MS to be target compound. Its chemical purity is higher than 99.0% and isotopic enrichment is higher than 98.4% 15N.

Key words： isotope-labeled; synthesis; N,N-dimethylaniline; characterization; methylation

参考文献

References

1 Zhou, X.-J; Wu, Z.-W. Chemical Industry and Engineering Progress. 1996, 1, 5. (in Chinese).

(周小建，吴祖望，化工进展，1996, 1, 5. )

2 Li, W.; Tao, K.-Y. Fine and Specialty Chemicals. 2002, 16, 21. (in Chinese).

(李伟，陶克毅，精细与专用化学品，2002, 16, 21.)

3 Fu, J.; Wu, K.-R. Acta Petrolel Sinca. 1990, 6(2), 51. (in Chinese).

（傅军，武克瑞，石油学报，1990，6(2)，51．）

4 Iranpoor N., Firouzabadi H., Nowrouzi N., Khalili D. Tetrahedron.2009, 6(19), 3893.

5 Chen, J.-R.; Li, R.-X.; Han; Y.-X; Li, X.-J. Chemical Research and Application. 1997, 9(1), 15. (in Chinese).

（陈骏如，李瑞祥，韩银仙，李贤均，化学研究与应用，1997，9(1)，15．）

6 Zhao, Y.; Foo , S.-W.; Saito, S. Angewandte Chemie. 2011, 123(13), 3062.

7 Horikawa, Y.; Uchino, Y.; Sako, T. Chemistry Letters..2003, 32(3), 232.

8 Kokai Tokkyo Koho, JP 6081153, 1985.

9 Chen, P.-Y.; Chu, S.-J.; Chen, M.-C.; Chang, N.-S. Lin, W.-C. US 4901752, 1989.

10 Chen, P.; Chen H.; Chu, H.; Chang, N.; Chuang, T. Studies in Surface Science and Catalysis. 1986, 28 , 739.

11 Binsch, G..; Lambert, J.B.; Roberts, B.W.; Roberts, J.D.; Journal of the American Chemical Society. 1964, 86 (24): 5564.

12 Fones, W.S. ; White, J. Arch. Biochem.,1949, 20, 118.

13 Billman, J.H.; Radike, A.; Mundy, B. Journal of the American Chemical Society. 1942, 64 (12): 2977.

14 Thomas, D.G.; Billman, J. H; Davis, C.E. Journal of the American Chemical Society. 1946, 68 (5)：895.

15 Sekera, V.C.; Marvel, C. Journal of the American Chemical Society. 1933, 55(1): 345.

16 Tan, Q-W; Wang, Y. Chemistry World. 1995, 36(4): 188. (in Chinese).

（田庆伟，王奕，化学世界，1995，36 (4)：188．）

17 Tan, Q-W. Contemporary Chemical Industry. 2002, 31 (4): 201. (in Chinese).

（田庆伟，当代化工，2002，31 (4)：201．）
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