Process for producing aminomethylated heterocyclic derivative

Details Process for producing aminomethylated heterocyclic derivative Process for producing aminomethylated heterocyclic derivative

2000-06-09

2001-12-04

Gerstl, Robert (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06326497

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a process for producing an aminomethyl-heterocyclic derivative which is useful as an intermediate to produce biologically active substances such as medicines and agricultural chemicals, with a good yield, while suppressing the formation of by-products.
BACKGROUND ART
In general, it is known that aminomethyl-heterocyclic derivatives such as aminomethyl-thiazoles are useful as intermediates to produce biologically active substances such as medicines and agricultural chemicals.
With respect to aminomethyl-thiazoles as one kind of such aminomethyl-heterocyclic derivatives, there is known a process for producing aminomethyl-thiazoles by reacting a chloromethyl-thiazole with an excess of aqueous ammonia solution so as to convert the chloro-group of the raw material into an amino group (KOKAI (Unexamined Patent Publication) No. Hei. 4-234864). However, in this process, in addition to the aminomethyl-thiazole as the desired product, there are inevitably produced the dimer and the trimer of the desired product which are attributable to a further reaction of the aminomethyl-thiazole per se with the chloromethyl-thiazole as the raw material. Therefore, this process is not advantageous, in view of the industrial practice thereof as well as in view of the protection of surrounding environment.
There is also known a process wherein halomethyl thiazole is reacted with potassium phthalimide, and the resultant product is further reacted with hydrazine (Published European Patent No. 302389). However, the potassium phthalimide is a relatively expensive reagent and, further, the production of waste at the time of the decomposition of the hydrazine causes an industrially or environmentally serious problem.
Further, there is also known a process wherein halomethyl thiazole is reacted with hexamethylene tetramine, and the resultant product is subsequently subjected to solvolysis by the use of mineral acid (KOKAI No. Hei. 4-234864). However, in this process, only one nitrogen atom among the four nitrogen atoms of the hexamethylene tetramine is consumed by the real reaction, and the remainder of the nitrogen atoms only cause waste. Therefore, this process is not advantageous both in view of industrial practice and in view of the environment.
DISCLOSURE OF INVENTION
An object of the present invention is to provide a production process which is capable of providing an aminomethyl-heterocyclic compound (such as aminomethyl-thiazoles), with a good yield while controlling the formation of by-products.
Another object of the present invention is to provide a production process which is capable of providing an aminomethyl-heterocyclic compound easily and at high purity.
As a result of earnest study, the present inventor has found that the reaction of a specific heterocyclic halide compound with ammonia in the presence of an aromatic aldehyde provides a desired aminated product, with a good yield, while effectively suppressing the formation of by-products such as the dimer and the trimer, although an unreacted halogenated compound is co-present with the free aminated product produced in the same reaction system.
The process for producing an aminomethyl-heterocyclic compound according to the present invention is based on above discovery and, more specifically, it is a process wherein a heterocyclic halide compound represented by a general formula (I):
T—CH
2
—Y  (I)
(wherein T denotes a heterocyclic group, and Y denotes a chlorine atom, bromine atom or iodine atom),
is reacted with ammonia in the presence of an aromatic aldehyde represented by a general formula (II):
A—CHO  (II)
(wherein A denotes an aromatic group),
to thereby produce a Schiff base (protected aminated product) represented by a general formula (III):
T—CH
2
—N═CH—A  (III).
According to the present inventor's knowledge, the reason why the above-mentioned production process according to the present invention can provide a desired Schiff base in good yield while effectively suppressing the formation of by-products such as the dimer and the trimer, although an unreacted halogenated product is co-present with the free aminated product produced in the same reaction system, is presumed to be that the free aminated product which has been produced by the reaction of the heterocyclic halide compound as the raw material with ammonia is rapidly reacted with an aromatic aldehyde to provide the Schiff base in preference to the reaction of the free aminated product with the halide, and therefore the formation of the by-products such as the dimer and the trimer which can be produced by a further reaction of the free aminated compound as the product with the halide as the raw material is effectively prevented, and hence the desired Schiff base is provided in good yield.


REFERENCES:
patent: 5180833 (1993-01-01), Uneme et al.
patent: 5756769 (1998-05-01), Seko et al.
patent: 4-5262 (1992-01-01), None
patent: 5043504 (1993-02-01), None
patent: 07-188170 (1995-07-01), None

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