DD260698A1 - METHOD FOR THE PRODUCTION OF BIS-OXAZOLIUM SALTS - Google Patents

Abstract

With the invention is to be achieved to make the hitherto unknown bis-oxazolium salts in a simple manner in high purity and with good yields. This is done according to the invention in such a way that a-aminoketones are reacted with Biscarbonsaeurederivaten in the presence of a condensing agent and a metal salt of a complex acid to the bis-oxazolium salts. Such compounds can gain importance as fluorescence or laser dyes, as intermediates for the production of dyes and spectral sensitizers and for biologically active compounds.

Description

where R ¹ and R ² , which may be identical or different, denote hydrogen, an unsubstituted or substituted aryl or heteroaryl radical and R ^{3 is} a simple alkyl radical having two to ten carbon atoms or an unsubstituted or substituted aryl radical, with bifunctional carboxylic acid chlorides of the general Formula IV,

Cl-C-R ^ -C-

CL ti Ii ^IV

0 0

wherein R ^{4 represents} an unsubstituted or substituted arylene radical, an alkyl group of chain length one to four or a direct bond between the carbonyl carbon atoms, in the presence of a condensing agent such as acetic anhydride, POCl ₃ , polyphosphoric acid or H ₂ SO ₄ and in the presence of a metal salt of a complex acid , such as NaCIO ₄ or NaBF ₄ , to the bis-oxazolium salts of general structure I

wherein R ¹ , R ² , R ³ and R ^{4 have} the abovementioned meaning and Y is the anion of the metal salt of the complex acid, that is about CIO ₄ or BFJ, are reacted.

embodiment

The invention will be explained in more detail below using the example of the preparation of 1,4-bis (2-methyl-4,5-diphenyl-oxazol-3-ylium) benzene perchlorate.

0.1 mol of 1,4-phenylene-bis-aminodeoxybenzoin are heated to boiling with 0.1 mol of Mg (CIO ₄ ) 2 in 1 mol of acetic anhydride. Allow to cool to 60 ° C, add 5 ml of concentrated H ₃ PO ₄ and allow to cool. The precipitate is filtered off, washed with a little methanol and recrystallized from nitromethane. This gives 0.07 mol of the above bis-oxazolium salt with a melting point of 300 ⁰ C.

Claims (1)

A process for the preparation of bis-oxazolium salts of type I, characterized in that a-aminoketones with Biscarbonsaurederivaten in the presence of a condensing agent such as acetic anhydride, POCl ₃ , polyphosphoric acid or H ₂ SO ₄ and in the presence of a metal salt of a complex acid such as NaCIO ₄ or NaBF ₄ , to the bis-oxazolium salts of type I in which R ¹ , R ² and R ^{3 are} unsubstituted or substituted aryl radicals, R ^{2 can} also be hydrogen and R ^{4 is} a direct bond, an arylene or alkylene radical and Y - each is the anion of the metal salt of the complex acid, are reacted. Field of application of the invention The invention relates to a process for the preparation of bis-oxazolium salts of the type I. R π O R- ''' 2Y Such compounds may gain importance as fluorescence or laser dyes, as intermediates for the preparation of dyes and spectral sensitizers and for biologically active compounds. Characteristic of the known technical solutions Bis-oxazolium salts of type I are unknown. Object of the invention The aim of the invention is to produce the hitherto unknown Bisoxazoliumsalze in a simple manner and in high purity with good yields. Explanation of the essence of the invention The invention has for its object to produce the previously unknown bis-oxazolium salts in a simple manner and in high purity with good yields. According to the invention this object is achieved in that a-aminoketones of the general formula III,