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

doi:10.6023/cjoc1108121

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (01): 145-148.DOI: 10.6023/cjoc1108121 Previous Articles Next Articles

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稳定同位素标记¹⁵N-N,N-二甲基苯胺的合成

杨维成^a, 齐庆瑞^b, 刘卫霞^a, 李美华^a, 罗勇^a

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 发布日期:2011-09-30
通讯作者: 罗勇 E-mail:real-luoyong@hotmail.com
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.

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

Yang Weicheng^a, Qi Qingrui^b, Liu Weixia^a, Li Meihua^a, Luo Yong^a

a Research & Development Center, Shanghai Research Institute of Chemical Industry, Shanghai 200062;
b Branch of Professional Education, Xinjiang Normal University, Urumqi 830046

Received:2011-08-12 Revised:2011-09-15 Published:2011-09-30
Contact: Yong LUO E-mail:real-luoyong@hotmail.com
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).

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

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Yang Weicheng, Qi Qingrui, Liu Weixia, Li Meihua, Luo Yong . Synthesis of Isotope-Labeled ¹⁵N-N,N-Dimethylaniline[J]. Chin. J. Org. Chem., 2012, 32(01): 145-148.

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稳定同位素标记¹⁵N-N,N-二甲基苯胺的合成

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

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稳定同位素标记15N-N,N-二甲基苯胺的合成