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Utilize methylene self-transfer reaction to prepare the method for n-methylation urotropine salt

A technology of urotropine and methyl, which is applied in the field of high nitrogen heterocyclic compound preparation chemistry, can solve the problems of limiting the preparation and application of methylated urotropine salt, high price, high toxicity and the like

Inactive Publication Date: 2017-03-08
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, those active methyl compounds are generally expensive, and some are highly toxic, which limits the preparation and application of methylated urotropine salts

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add hundreds of milliliters of absolute ethanol to about 100 grams of urotropine, stir at room temperature, and most of them dissolve. Control the temperature not higher than 25°C; add an equivalent amount of concentrated hydrochloric acid dropwise under stirring to form a white, light solid. After the addition of concentrated hydrochloric acid, continue to stir for several hours; filter; wash the solid with absolute ethanol, and dry under reduced pressure to obtain urotropine hydrochloride with a yield of about 90%. M.p.188-190℃. 1 H NMR (300MHz,D 2 O): δ4.64s; (300MHz, DMSO-d 6 ): 4.73s.

Embodiment 2

[0027] The urotropine hydrochloride prepared in Example 1 was mixed with water and heated to reflux for several hours, then rotary evaporated to dryness. remnants 1 H NMR spectrum showed that the product was a mixture of unreacted urotropine hydrochloride and N-methylated urotropine chloride etc. Pure N-methylated urotropine chloride: 1 H NMR (D 2 O): 4.85 (s, 6H), 4.53 (d, J = 12, 3H), 4.33 (d, J = 12, 3H), 2.41 (s, 3H); (DMSO-d 6 ): 5.03 (s, 6H), 4.59 (d, J = 12, 3H), 4.45 (d, J = 12, 3H), 2.33 (s, 3H).

Embodiment 3

[0029] Except that ethanol was used instead of water, urotropine hydrochloride was reacted under the same conditions as in Example 2, and N-methylated urotropine chloride was also obtained.

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PUM

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Abstract

The invention provides a method for preparing an N-methylated urotropin salt. The method comprises the step of directly converting the protonated urotropin salt generated by urotropin and protonic acid to the N-methylated urotropin salt under a proper condition. The principle is as follows: urotropin is protonated to generate tertiary amine cations containing N-H bonds; the generation of the cations activates methylene on an urotropin framework connected with protonated nitrogen atoms, then the reactions of chain scission, transfer and N<+>-H bond insertion are carried out under proper conditions, finally N-methylated urotropin cations are generated, and during the methylene transfer reaction, anions generally do not participate in the reaction. The preparation method does not need other methylation reagents and relates to few chemical species; the raw materials are low in price and easily available; the preparation process is simple and the treatment is convenient; the method is a highly-greened method for preparing the N-methylated urotropin salt.

Description

technical field [0001] The invention relates to a method for preparing N-methylurotropine salt by utilizing methylene self-transfer reaction, and belongs to the field of preparation chemistry of high nitrogen heterocyclic compounds. Background technique [0002] As we all know, hexamethylenetetraamine (hexamethylenetetraamine, hexamine) is a cheap and easy-to-obtain high-nitrogen heterocyclic chemical raw material. S.G.; Turankar, A.V.; Sontakke, S.D. Medical Hypotheses 2013, 80, 507. Yao, Joseph, D.C.; Moellering, Robert C., Jr. Edited by Versalovic, James, Manual of Clinical Microbiology, 10th Edition, 2011, 1, 1043-1081 .Bendewald, Margo J.; Farmer, Sara A.; Davis, Mark D.P. Dermatitis 2010, 21, 33-40. Dowling, Patricia M. Edited by Giguere, Steeve Antimicrobial Therapy in Veterinary Medicine 4th Edition, 2006, 285-300. Mitscher , Lester A.; Lemke, Thomas L.; Gentry, Elmer J. Edited by Lemke, Thomas L.; Williams, David A Foye's Principles of Medicinal Chemistry 6th Editi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/18
CPCC07D487/18
Inventor 单自兴
Owner WUHAN UNIV