IL34778A

IL34778A - Process for the production of n-trityl-imidazoles and-triazoles

Info

Publication number: IL34778A
Application number: IL34778A
Authority: IL
Original assignee: Bayer Ag
Priority date: 1969-08-09
Filing date: 1970-06-23
Publication date: 1972-07-26
Also published as: GB1256476A; IL34778A0; FR2056725A5; DE1940627A1; BR6915158D0; NL7011514A; BE754506A; CH535240A; AT296297B

Description

for the production of A The present invention relates to an unobvious process for the production of certain and some of which are new and some of which are known as having good properties against and fungi and yeasts and also fungicidal properties against phytopathogenic fungi Belgian Patent Specification It is known Giesemann and 9 that are obtained by reacting the silver salts of imidazoles with loromethane in boiling benzene according to Patent Specification reacting sodium or silver salts of imidazoles with l chlorides or bromides in suitable organic solvents at temperatures between and can be prepared according to Belgian Patent Specification by reacting halides with silver sodium salts of imidazoles or by reacting imidazoles with triphenylmethyl Analogous reactions with triazoles have hitherto not been the known processes have a number of the silver salts of imidazoles must be separately prepared and are expensive starting Giesemann and Halschke state that the resulting the reaction described by them are only obtained in yields between and of The present invention provides a process for the production of of the general formula in which j denotes an yl 1 radical may be substituted by or more lower alkyl ary halogen atoms or nitro X may have different meanings in the various rings stands dialkylamino thio alkylsulphoxy or is 1 or n is 1 or and o is 1 or in which a compound of the general formula R Hal in which R has the same meanin as and is with a tri in which n and o have the same meaning as Any lower alkyl radicals in R contain preferably 1 4 carbon any aryl radicals in R contain up to preferably 6 carbon any halogen in R is preferably contains an or aryloxy this normally contains up to preferably carbon When is halogen it may be bromine or When X is it is preferably a Suitable polar organic solvents are primarily those which have a good dissolving power for examples are dimethyl acid triamide and dimethyl The magnesium halides of imidazole and triazole of the formula may be prepared by adding an ethereal solution of a Grignard such as bromide or magnesium which has been obtained in a conventional to an equimolar amount of the heterocyclic component dissolved in the polar organic diluent imidazole in dimethyl if necessary while The ether used for preparing the Grignard compound is subsequently drawn in a vacuum so that a solution of the halide compound in the polar solvent dimethyl is obtained as the The halides and imidazoles used as starting compounds are known or may be obtained by known The reaction of the halide compound with the halide is carried out at temperatures between about and preferably at about to When carryin out the process according to the the starting materials preferabl reacted in a molar ratio approximately The reaction times depend upon the reaction and are generally from 3 to 24 For working the mixture may be diluted with an aqueous ammonium chloride solution and the compound of formula which is insoluble in water may be isolated if A clear colourless solution is thus from which the salt partially crystallises after prolonged standing at room It redissolves when heated to about Reaction with trityl g trityl chloride and the solution containing mol bromide are heated at about for 1 allowed to stand and mixed with an ammonium chloride and the solids are off with The filter residue is washed with an ammonium chloride solution and and In this there are obtained 31 g of a crude product of 200 Recrystallisation from yields g in the form of colourless crystals of The compounds of the following Examples are obtained in an analogous wa 225 232 228 230 140 145 128 149 114 152 185 174 160 170 164 130 142 imidazole 199 imidazole 144 imidazole 116 imidazole 150 imidazole 140 119 163 187 129 134 162 imidazole 139 140 219 triazole 211 triaaole 201 203 the substances listed the compounds 24 to are insufficientOCRQuality

Claims

what we claim is :- 1. A process for the production of N-trityl-imidazoles and N-trityl-triazoles of the general formula in whiqh R denotes imidazol-l-yl, 1,2,4-triazol-l-yl or

1. ,2,3-triazol-l-yl radical which may be substituted by one or more lower alkyl radicals, aryl radicals, halogen atoms or nitro groups: X (which may have different meanings in the various rings) stands for hydrogen, OH, halogen, nitro, CN, amino, dialkylamino , haloalkyl, alkyl, aryl, thio alkoxy, aryloxy, alkylme-rea-pt-e-, alkylsulphoxy or alkylsulphonyl; m is 1 or 2, n is 1 or 2, and o is 1 or 2, in which a compound of the general formula R - g - Hal in which R has the same meaning as above, and Hal stands for chlorine, bromine or iodine, is reacted in a polar organic solvent at 0 - 120°C triphenyl-methyl halide of the general formula in which. X, Hal, m, n and o have the same meaning as above.

2. A process according to claim 1 in which the reaction is carried out at 20-50°C.

3. A process according to claim 1 or 2 in which the polar, solvent is dimethyl formamide,dimethyl sulphoxide or hexamethyl phosphoric acid triamide.

4. A process according to any of claims 1-3 in which the reactants are reacted in a molar ratio of approximately 1:1.

5. A process according to any of claims 1-4 in which, after the reaction, the reaction mixture is diluted with aqueous ammonium chloride solution and the compound of formula (I) is isolated. .

6. A process according to any of claims 1-5 in which the compound of formula (II) is prepared in situ by reacting an ethereal solution of an appropriate Grignard compound, with an equimolar amount of the appropriate imidazolyl or triazolyl compound dissolved in the polar solvent, and drawing off the ether by vacuum so as to leave the compound of formula (II) dissolved in the polar solvent.

7. A process according to any of claims 1-6 i which any lower alkyl radicals in R contain 1-4 carbon atoms, any aryl radicals in K contain 6 carbon atoms, any halogen in R is 1-3 carbon atoms or an aryl or aryloxy radical with 6 carbon atoms, or X is hydrogen, halogen, OH, nitro, CN, amino or C ^

8. A process for the production of a compound of formula (I), substantially as hereinbefore described in the Examples.

9. Compounds of formula (I) whenever prepared by a process according to any of claims 1 - 8.