Method for substitution of an amino group of a primary amine by

Details Method for substitution of an amino group of a primary amine by Method for substitution of an amino group of a primary amine by

1996-11-20

1998-09-22

Gerstl, Robert

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D27732

Patent

active

058115552

ABSTRACT:
This invention relates to methods for substitution of an amino group of a heterocyclic primary amine by a chlorine atom and synthesis of 2-chloro-5-methylthiazole and its derivatives by application thereof.
Typically, a heterocyclic primary amine and sodium nitrite are caused to react in the presence of hydrochloric acid, followed by heating the formed diazonium base at 30.degree.-100.degree. C. in the presence of an equimolar or more of hydrochloric acid to substitute the amino group by the chlorine atom. Further, 2-amino-5-methylthiazole and sodium nitrite are caused to react in the presence of hydrochloric acid, followed by heating the formed diazonium base at 30.degree.-100.degree. C. in the presence of an equimolar or over of hydrochloric acid to give 2-chloro-5-methylthiazole. Then, the resultant 2-chloro-5-methylthiazole is caused to react with a chlorinating agent to give 2-chloro-5-chloro-methylthiazole.

REFERENCES:
patent: 3461125 (1969-08-01), Kollonitsch
Nagahara, J. Med. Chem. 33 (1) 407, 1990.
McLean, John, "Reactions of Certain Thiazoles and Glyoxalines with Picryl Chloride and 2:4-Dinitrochlorobenzene", 1942, pp. 383-386, Journal Of The Chemical Society.

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