IL34778A - Process for the production of n-trityl-imidazoles and-triazoles - Google Patents
Process for the production of n-trityl-imidazoles and-triazolesInfo
- Publication number
- IL34778A IL34778A IL34778A IL3477870A IL34778A IL 34778 A IL34778 A IL 34778A IL 34778 A IL34778 A IL 34778A IL 3477870 A IL3477870 A IL 3477870A IL 34778 A IL34778 A IL 34778A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- process according
- formula
- halogen
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 12
- -1 imidazol-l-yl Chemical group 0.000 claims description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- NPZDCTUDQYGYQD-UHFFFAOYSA-N 1-tritylimidazole Chemical class C1=NC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NPZDCTUDQYGYQD-UHFFFAOYSA-N 0.000 claims 1
- WQQJRYCRMJDNIT-UHFFFAOYSA-N 1-trityltriazole Chemical class N1=NC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WQQJRYCRMJDNIT-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
- 150000002460 imidazoles Chemical class 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KIIUTKAWYISOAM-UHFFFAOYSA-N silver sodium Chemical class [Na].[Ag] KIIUTKAWYISOAM-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 (9)
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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691940627 DE1940627A1 (en) | 1969-08-09 | 1969-08-09 | Process for the preparation of N-tritylimidazoles and -triazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34778A0 IL34778A0 (en) | 1970-08-19 |
| IL34778A true IL34778A (en) | 1972-07-26 |
Family
ID=5742399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34778A IL34778A (en) | 1969-08-09 | 1970-06-23 | Process for the production of n-trityl-imidazoles and-triazoles |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT296297B (en) |
| BE (1) | BE754506A (en) |
| BR (1) | BR6915158D0 (en) |
| CH (1) | CH535240A (en) |
| DE (1) | DE1940627A1 (en) |
| FR (1) | FR2056725A5 (en) |
| GB (1) | GB1256476A (en) |
| IL (1) | IL34778A (en) |
| NL (1) | NL7011514A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2407305C2 (en) * | 1974-02-15 | 1984-06-28 | Bayer Ag, 5090 Leverkusen | Triphenyl-1,2,3-triazol-1-yl-methanes, process for their preparation and their use as fungicides |
| US4227004A (en) | 1979-01-02 | 1980-10-07 | Ici Americas Inc. | Synthesis of substituted 1-aralkyl-1H-v-triazoles |
| US4398942A (en) | 1980-12-22 | 1983-08-16 | Rohm And Haas Company | Herbicidally-active phenylacetonitriles |
-
0
- BE BE754506D patent/BE754506A/en unknown
-
1969
- 1969-08-09 DE DE19691940627 patent/DE1940627A1/en active Pending
- 1969-12-15 BR BR215158/69A patent/BR6915158D0/en unknown
-
1970
- 1970-06-17 CH CH919570A patent/CH535240A/en not_active IP Right Cessation
- 1970-06-23 IL IL34778A patent/IL34778A/en unknown
- 1970-08-04 NL NL7011514A patent/NL7011514A/xx unknown
- 1970-08-06 GB GB1256476D patent/GB1256476A/en not_active Expired
- 1970-08-07 AT AT720470A patent/AT296297B/en not_active IP Right Cessation
- 1970-08-07 FR FR7029228A patent/FR2056725A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1256476A (en) | 1971-12-08 |
| FR2056725A5 (en) | 1971-05-14 |
| AT296297B (en) | 1972-02-10 |
| DE1940627A1 (en) | 1971-02-11 |
| NL7011514A (en) | 1971-02-11 |
| IL34778A0 (en) | 1970-08-19 |
| BE754506A (en) | 1971-02-08 |
| BR6915158D0 (en) | 1973-04-10 |
| CH535240A (en) | 1973-03-31 |
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