JPH01226879A - Production of aminotriazine derivative - Google Patents

Abstract

PURPOSE:To readily obtain an amino-1,3,5-triazine compound useful as medicines, agricultural chemicals, dyes, etc., in good yield from an inexpensive and stable compound as a raw material without using a solvent, by reacting a formamide with a di-substituted cyanamide under a high pressure. CONSTITUTION:One molecule of a formamide expressed by formula I (R1 is alkyl, aryl, aralkyl or H), such as formamide, is reacted with 3mol. of a di- substituted cyanamide expressed by formula II (R2 and R3 are alkyl or together form a ring), such as 1-piperidinecarbonitrile, at 50-250 deg.C under >=1,000kg/cm<2>, normally as high as 1,000-9,000kg/cm<2> to afford the aimed compound expressed by formula III, such as 2-amino-4,6-di(1-piperidine)1,3,5-triazine. Furthermore, since di-substituted formamides having a di-substituted amino group expressed by formula IV formed as a by-product act as a solvent in completing the reaction for increasing the amount of the aimed compound, use of a solvent in the reaction system is not required.

Description

DETAILED DESCRIPTION OF THE INVENTION This invention relates to a method for producing an amino-1,3°5-triazine compound by reaction with a substituted cyanamide represented by the general formula (wherein R1, R, and R3 are the same as above).

[Prior art]

It is known that amino-1,3,5-triazine compounds are usually synthesized using cyanuric chloride and amines as raw materials, except in the case of melamine. The amino-1,3°5-triazine compounds thus obtained are widely used in agricultural chemicals, medicines, dyes, and the like.

However, in this reaction, cyanuric chloride as a raw material absorbs moisture and tends to undergo dehydrochloric acid decomposition, and hydrochloric acid is also produced by the substitution reaction with amines, requiring post-treatment after the reaction.2, 4. When the amino groups in the 6-position are not the same, there is a drawback that a large number of steps are required because the reaction conditions are changed and different amines are used for successive substitution.

[Objective] The present invention provides a new reaction that does not have the above-mentioned drawbacks found in the synthesis of amino-1,3,5-triazine compounds.

〔composition〕

The present inventors have developed various methods for synthesizing amino-1,3,5-)-lyazine compounds that do not have the above-mentioned drawbacks, using compounds that have a relatively simple structure, are inexpensive, and are stable. As a result of investigation, when formamide and disubstituted cyanamide are reacted under a pressure of 1000 kg/- or more, 1,3.5 with formamide's amino group at the 2-position and cyanamide's disubstituted amino group at the 4- and 6-positions. - It has been found that a triazine compound can be obtained in good yield.

That is, in the present invention, one molecule of formamide is produced. This by-product disubstituted cyanamide acts as a solvent at the end of the reaction when the amount of solid product amino-1,3,5-triazine increases, so it has the advantage that no solvent needs to be added to the reaction system. In addition, it is also useful as a new synthetic method for such disubstituted formamides.

As the formamide used in the present invention, in addition to unsubstituted formamide, monosubstituted formamide such as N-phenylformamide, N-benzylformamide, and N-methylformamide can be used. On the other hand, examples of the disubstituted cyanamide include dimethyl cyanamide, diethyl cyanamide, and the like, as well as cyclic cyanamides such as 1-piperidine carbonitrile, 1-pyrodine carbonitrile, and 1-morpholine carbonitrile.

Although it is not necessary to use a reaction accelerator or a solvent, there is no problem in using a compound inert to the reaction such as disubstituted formamide as a solvent.

〔Example〕

Next, the present invention will be explained in more detail with reference to Examples.

Note that the parts shown in each example represent parts by weight, and the % regarding yield is the theoretical yield regarding the disubstituted cyanamide.

Example 1 3.4 parts of formamide and 24.7 parts of 1-piperidine carbonitrile (molar ratio 1:3) were encapsulated in a Ceflon capsule and housed in a high-pressure reaction tube to produce approximately 3000 kg/a.
After pressurizing to #, the reaction tube was externally heated to bring the internal temperature to 160℃.
Raise the temperature to and further pressure to separate the crystalline solid product,
Recrystallization from methanol or isopropyl ether gives 2-amino-4,6-di(1-piperidine)-1,
11.7 parts of 3,5-triazine (yield 6o%) were obtained.

Examples 2 to 16 Same method as Example 1, raw material mixing molar ratio 1:3, reaction pressure 4000 kg/cd, reaction temperature 160°C, reaction time 2
The following 15 combinations of formamide and disubstituted cyanamide were reacted under conditions of 0 hours.

The yields of the 15 types of aminotriazines obtained were displayed.

Claims (1)

[Claims] (1) Formamide represented by the general formula HCONHR_1 (in the formula, R_1 is an alkyl group, aryl group, aralkyl group, or hydrogen atom) and the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (in the formula, R_2 and R_3 are It is an alkyl group, and further R_
Including those having a cyclic structure in which 2 and R_3 are bonded. )
disubstituted cyanamide represented by 1000kg/cm
^2 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1, R_2, R_3 are the same as above) of 1,3,5-triazine Production method.