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Manufacturing method of N-methylene substituted methylamine polymer and triazine derivative

A manufacturing method and a polymer technology, applied in the formation/introduction of amino groups, organic chemistry, etc., can solve the problems of large amount of solvent, difficult handling, complicated operation, etc., and achieve high yield, simplicity, yield, and low cost Effect

Inactive Publication Date: 2014-03-19
NIPPON SODA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, these manufacturing methods are not necessarily industrially effective methods
That is, in the first method, because the raw material needs to use relatively expensive potassium phthalimide, it cannot be said to be a preferable method in terms of economy.
In addition, since it is necessary to remove phthalazine from the reaction solution with hydrazine, the post-treatment operation is complicated.
In the second method, the amount of solvent used in the reaction is large, and relatively expensive hexamethylenetetramine is used in a large amount, so it cannot be said that it is an economically preferable method.
In addition, in this method, the produced 2-chloro-5-pyridylmethylhexamethylenetetraammonium chloride is temporarily isolated and then hydrolyzed, so there is a problem of complicated operation.
The third method has the problem that the isolated N-methylene-2-chloro-5-pyridylmethylamine is unstable and difficult to handle

Method used

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  • Manufacturing method of N-methylene substituted methylamine polymer and triazine derivative
  • Manufacturing method of N-methylene substituted methylamine polymer and triazine derivative
  • Manufacturing method of N-methylene substituted methylamine polymer and triazine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0114] (Example 1) Production of (2-chloropyridin-5-yl)methanamine (1)

[0115] Add 5ml of water and 5ml of toluene to 3.02g (10mmol) of (2-chloropyridin-5-yl) hexamethylenetetraammonium chloride (I-1), adjust the pH to 10~ with 28% aqueous sodium hydroxide solution 11 while stirring at 60°C for 7 hours.

[0116] 4 ml of toluene was added to the reaction solution, and the toluene layer was obtained by separation. 7 g of concentrated hydrochloric acid was added to the toluene layer, and the aqueous layer was separated to obtain one type of hydrochloride of N-methylene-2-chloro-3-pyridylmethylamine polymer (II-1). or a mixture of two or more.

[0117] 3.2 g of methanol was added to the separated aqueous layer and treated at 60° C. for 3 hours to obtain (2-chloropyridin-5-yl)methanamine (III-1) hydrochloride as an aqueous solution. As a result of HPLC analysis, the yield was 1.21 g (85% yield).

Embodiment 2）

[0118] (Example 2) Production of (2-chloropyridin-5-yl)methanamine (2)

[0119] Add 5ml water and 1ml toluene to 1.62g (10mmol) 2-chloro-5-(chloromethyl)pyridine (Ⅺ-1) and 1.48g (10mmol) hexamethylenetetramine, add 28% sodium hydroxide aqueous solution The pH was adjusted to 10-11 while stirring at 60° C. for 7 hours.

[0120] 4 ml of toluene was added to the reaction solution, and the toluene layer was obtained by separation. 7 g of concentrated hydrochloric acid was added to the toluene layer, and the aqueous layer was separated to obtain one type of hydrochloride of N-methylene-2-chloro-3-pyridylmethylamine polymer (II-1). or a mixture of two or more.

[0121] 3.2 g of methanol was added to the separated aqueous layer and treated at 60° C. for 3 hours to obtain (2-chloropyridin-5-yl)methanamine (III-1) hydrochloride as an aqueous solution. As a result of HPLC analysis, the yield was 1.28 g (90% yield).

Embodiment 3）

[0122] (Example 3) Production of (2-chloropyridin-5-yl)methanamine (3)

[0123] Add 5ml water and 1ml toluene to 1.62g (10mmol) 2-chloro-5-chloromethylpyridine (XI-1) and 0.7g (5mmol) hexamethylenetetramine, adjust the pH with 28% aqueous sodium hydroxide solution While adjusting to 10-11, it stirred at 60 degreeC for 7 hours.

[0124] 4 ml of toluene was added to the reaction solution, and the toluene layer was obtained by separation. 7 g of concentrated hydrochloric acid was added to the toluene layer, and the aqueous layer was separated to obtain an aqueous layer containing one or a mixture of two or more hydrochlorides of the pyridylmethylimine compound (II-3).

[0125] 3.2 g of methanol was added to the separated aqueous layer and treated at 60° C. for 3 hours to obtain (2-chloropyridin-5-yl)methanamine (III-1) hydrochloride as an aqueous solution. As a result of HPLC analysis, the yield was 1.26 g (89% yield).

[0126] As mentioned above, compared with Example 2, even...

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Abstract

The invention relates to a manufacturing method of one of or a mixture of more than two of N-methylene substituted methylamine polymer as shown in the following formula (II), which is characterized in that one of or a mixture of more than two of N-methylene substituted methylamine polymer as shown in the formula (II) are obtained by reacting hexamethylene tetramine compounds shown in formula (I) with alkali. In the formula (I), A represents any organic group of an alkyl or heterocyclic group, or the organic group with a substituent group; R represents a hydrogen atom, or any organic group of an alkyl or heterocyclic group, or the organic group with a substituent group; L represents a halogen atom, an alkyl sulfonyl oxy group with a carbon atom number of 1-20, a halogenated alkyl sulfonyl oxy group with a carbon atom number of 1-20, or substituted or unsubstituted aryl sulfonyl oxy group. In the formula (II), A and R represent the same as the above, and n represents an integer of 2-20.

Description

[0001] (This application is a divisional application of the patent application with the filing date of April 24, 2007, the application number of 200780052685.2, and the title of the invention entitled "Manufacturing Method of Substituted Methylamine Compounds and Triazine Derivatives".) technical field [0002] The present invention relates to a simple, high-yield, and low-cost method for producing substituted methylamine compounds such as pyridylmethylamine compounds useful as production intermediates for pesticides and medicines, and N-methylene-substituted methylamine compounds as production intermediates thereof. Methylamine Polymer. Background technique [0003] Substituted methylamine compounds, for example, pyridylmethylamine compounds such as 2-chloro-5-pyridylmethylamine are compounds useful as intermediates for the production of agricultural chemicals and pharmaceuticals. [0004] Conventionally, as a method for producing pyridylmethylamine compounds, it is known t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07D401/14C07B43/04
CPCC07D213/61C07D401/14C08G73/0213
Inventor 柴田泰史今川务
Owner NIPPON SODA CO LTD