DE1940628A1 - Verfahren zur Herstellung von N-Tritylimidazolen und -triazolen - Google Patents
Verfahren zur Herstellung von N-Tritylimidazolen und -triazolenInfo
- Publication number
- DE1940628A1 DE1940628A1 DE19691940628 DE1940628A DE1940628A1 DE 1940628 A1 DE1940628 A1 DE 1940628A1 DE 19691940628 DE19691940628 DE 19691940628 DE 1940628 A DE1940628 A DE 1940628A DE 1940628 A1 DE1940628 A1 DE 1940628A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- diphenyl
- triazoles
- alkyl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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 title description 2
- -1 alkyl radicals Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 2
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 244000037640 animal pathogen Species 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 244000052637 human pathogen Species 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE754570D BE754570A (fr) | 1969-08-09 | Procede de fabrication de n-triphenylmethylimidazoles et de n-triphenylmethyltriazoles a l'aide de derives de trimethylsilyle | |
| DE19691940628 DE1940628A1 (de) | 1969-08-09 | 1969-08-09 | Verfahren zur Herstellung von N-Tritylimidazolen und -triazolen |
| BR215156/69A BR6915156D0 (pt) | 1969-08-09 | 1969-12-15 | Processo para a preparacao de n-tritilimidazois e-triazoi |
| CH919370A CH537931A (de) | 1969-08-09 | 1970-06-17 | Verfahren zur Herstellung von N-Tritylimidazolen und -triazolen |
| IL34780A IL34780A (en) | 1969-08-09 | 1970-06-23 | Process for the production of n-trityl-imidazoles and-triazoles |
| JP6222070A JPS5417741B1 (enrdf_load_stackoverflow) | 1969-08-09 | 1970-07-17 | |
| NL7011515A NL7011515A (enrdf_load_stackoverflow) | 1969-08-09 | 1970-08-04 | |
| CA089,843A CA948631A (en) | 1969-08-09 | 1970-08-04 | Preparation of n-trityl-imidazoles and n-trityl-triazoles |
| GB1264598D GB1264598A (enrdf_load_stackoverflow) | 1969-08-09 | 1970-08-06 | |
| AT720370A AT294833B (de) | 1969-08-09 | 1970-08-07 | Verfahren zur Herstellung von N-Tritylimidazolen und -triazolen |
| FR7029229A FR2056726A5 (enrdf_load_stackoverflow) | 1969-08-09 | 1970-08-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691940628 DE1940628A1 (de) | 1969-08-09 | 1969-08-09 | Verfahren zur Herstellung von N-Tritylimidazolen und -triazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1940628A1 true DE1940628A1 (de) | 1971-02-11 |
Family
ID=5742400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691940628 Pending DE1940628A1 (de) | 1969-08-09 | 1969-08-09 | Verfahren zur Herstellung von N-Tritylimidazolen und -triazolen |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5233048A (en) * | 1989-12-21 | 1993-08-03 | Bayer Aktiengesellschaft | Triarylmethane color formers |
-
0
- BE BE754570D patent/BE754570A/xx unknown
-
1969
- 1969-08-09 DE DE19691940628 patent/DE1940628A1/de active Pending
- 1969-12-15 BR BR215156/69A patent/BR6915156D0/pt unknown
-
1970
- 1970-06-17 CH CH919370A patent/CH537931A/de not_active IP Right Cessation
- 1970-06-23 IL IL34780A patent/IL34780A/xx unknown
- 1970-07-17 JP JP6222070A patent/JPS5417741B1/ja active Pending
- 1970-08-04 NL NL7011515A patent/NL7011515A/xx unknown
- 1970-08-04 CA CA089,843A patent/CA948631A/en not_active Expired
- 1970-08-06 GB GB1264598D patent/GB1264598A/en not_active Expired
- 1970-08-07 FR FR7029229A patent/FR2056726A5/fr not_active Expired
- 1970-08-07 AT AT720370A patent/AT294833B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5233048A (en) * | 1989-12-21 | 1993-08-03 | Bayer Aktiengesellschaft | Triarylmethane color formers |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6915156D0 (pt) | 1973-02-20 |
| BE754570A (fr) | 1971-02-08 |
| JPS5417741B1 (enrdf_load_stackoverflow) | 1979-07-02 |
| IL34780A (en) | 1972-07-26 |
| IL34780A0 (en) | 1970-08-19 |
| NL7011515A (enrdf_load_stackoverflow) | 1971-02-11 |
| GB1264598A (enrdf_load_stackoverflow) | 1972-02-23 |
| AT294833B (de) | 1971-12-10 |
| CA948631A (en) | 1974-06-04 |
| FR2056726A5 (enrdf_load_stackoverflow) | 1971-05-14 |
| CH537931A (de) | 1973-06-15 |
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