DE1954706A1 - Verfahren zur Herstellung von Imidazolderivaten - Google Patents
Verfahren zur Herstellung von ImidazolderivatenInfo
- Publication number
- DE1954706A1 DE1954706A1 DE19691954706 DE1954706A DE1954706A1 DE 1954706 A1 DE1954706 A1 DE 1954706A1 DE 19691954706 DE19691954706 DE 19691954706 DE 1954706 A DE1954706 A DE 1954706A DE 1954706 A1 DE1954706 A1 DE 1954706A1
- Authority
- DE
- Germany
- Prior art keywords
- nitroimidazole
- derivatives
- methyl
- preparation
- mol
- 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 18
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000019253 formic acid Nutrition 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical class CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
- -1 aliphatic alcohols Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 150000004960 4-nitroimidazoles Chemical class 0.000 claims description 2
- 150000004958 5-nitroimidazoles Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical class NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- AJVVICBRFZXGEW-UHFFFAOYSA-N 6-propoxy-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(OCCC)C1O2 AJVVICBRFZXGEW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 230000001572 anti-trichomonad Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance 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
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU254468A YU32302B (en) | 1968-10-31 | 1968-10-31 | Postopek za pripravo imidazolnih derivatov |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1954706A1 true DE1954706A1 (de) | 1970-05-14 |
Family
ID=25558242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691954706 Pending DE1954706A1 (de) | 1968-10-31 | 1969-10-30 | Verfahren zur Herstellung von Imidazolderivaten |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT292693B (cg-RX-API-DMAC10.html) |
| BE (1) | BE740975A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1954706A1 (cg-RX-API-DMAC10.html) |
| YU (1) | YU32302B (cg-RX-API-DMAC10.html) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2933721A1 (de) * | 1978-09-26 | 1980-03-27 | Usui Kokusai Sangyo Kk | Material fuer eine leitung zum einspritzen von treibstoff unter hohem druck |
| EP0030332A1 (de) * | 1979-12-05 | 1981-06-17 | BASF Aktiengesellschaft | Verwendung von 2-Hydroxypropylimidazolen als öllösliche Korrosionsinhibitoren |
| EP0054974A1 (en) * | 1980-12-24 | 1982-06-30 | Sumitomo Chemical Company, Limited | Imidazolylpropanol compounds and their acid addition salts, and production and use thereof |
| EP0070798A3 (de) * | 1981-07-02 | 1983-06-01 | Ciba-Geigy Ag | Mikrobizide und wuchsregulierende Mittel |
| DE3602899A1 (de) * | 1986-01-31 | 1987-08-06 | Kloeckner Humboldt Deutz Ag | Kraftstoffleitung fuer hohe druecke |
| DE10303853A1 (de) * | 2003-01-30 | 2004-08-12 | Schmittersysco Gmbh | Zusammengesetzte Kraftstoff-Hochdruck-Metalleitung mit einem inneren und einem äußeren Rohrteil sowie Herstellungsverfahren dafür |
-
1968
- 1968-10-31 YU YU254468A patent/YU32302B/xx unknown
-
1969
- 1969-10-29 BE BE740975D patent/BE740975A/xx unknown
- 1969-10-29 AT AT10171/69A patent/AT292693B/de not_active IP Right Cessation
- 1969-10-30 DE DE19691954706 patent/DE1954706A1/de active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2933721A1 (de) * | 1978-09-26 | 1980-03-27 | Usui Kokusai Sangyo Kk | Material fuer eine leitung zum einspritzen von treibstoff unter hohem druck |
| EP0030332A1 (de) * | 1979-12-05 | 1981-06-17 | BASF Aktiengesellschaft | Verwendung von 2-Hydroxypropylimidazolen als öllösliche Korrosionsinhibitoren |
| EP0054974A1 (en) * | 1980-12-24 | 1982-06-30 | Sumitomo Chemical Company, Limited | Imidazolylpropanol compounds and their acid addition salts, and production and use thereof |
| EP0070798A3 (de) * | 1981-07-02 | 1983-06-01 | Ciba-Geigy Ag | Mikrobizide und wuchsregulierende Mittel |
| DE3602899A1 (de) * | 1986-01-31 | 1987-08-06 | Kloeckner Humboldt Deutz Ag | Kraftstoffleitung fuer hohe druecke |
| DE10303853A1 (de) * | 2003-01-30 | 2004-08-12 | Schmittersysco Gmbh | Zusammengesetzte Kraftstoff-Hochdruck-Metalleitung mit einem inneren und einem äußeren Rohrteil sowie Herstellungsverfahren dafür |
Also Published As
| Publication number | Publication date |
|---|---|
| YU32302B (en) | 1974-08-31 |
| BE740975A (cg-RX-API-DMAC10.html) | 1970-04-01 |
| YU254468A (en) | 1974-02-28 |
| AT292693B (de) | 1971-08-15 |
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