CH449631A - Verfahren zur Herstellung von 1,2,5-Imidazolderivaten - Google Patents
Verfahren zur Herstellung von 1,2,5-ImidazolderivatenInfo
- Publication number
- CH449631A CH449631A CH861765A CH861765A CH449631A CH 449631 A CH449631 A CH 449631A CH 861765 A CH861765 A CH 861765A CH 861765 A CH861765 A CH 861765A CH 449631 A CH449631 A CH 449631A
- Authority
- CH
- Switzerland
- Prior art keywords
- imidazole derivatives
- preparation
- general formula
- compound
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 10
- -1 amino, carboxyl Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002460 imidazoles Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- USHZVGQGQFAWLW-UHFFFAOYSA-N 2-hydroxyimino-3-oxobutanal Chemical compound CC(=O)C(C=O)=NO USHZVGQGQFAWLW-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 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
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH861765A CH449631A (de) | 1965-06-21 | 1965-06-21 | Verfahren zur Herstellung von 1,2,5-Imidazolderivaten |
| DK382965A DK107099C (da) | 1965-06-21 | 1965-07-24 | Fremgangsmåde til fremstilling af 5-nitro-imidazolderivater. |
| NL6608513A NL6608513A (enrdf_load_stackoverflow) | 1965-06-21 | 1966-06-20 | |
| NO16355766A NO117030B (enrdf_load_stackoverflow) | 1965-06-21 | 1966-06-20 | |
| IS1568A IS689B6 (is) | 1965-06-21 | 1966-06-20 | Aðferð til framleiðslu á 1-2-substituierten 5-nitroimidazolen. |
| SE843866A SE328297B (enrdf_load_stackoverflow) | 1965-06-21 | 1966-06-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH861765A CH449631A (de) | 1965-06-21 | 1965-06-21 | Verfahren zur Herstellung von 1,2,5-Imidazolderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH449631A true CH449631A (de) | 1968-01-15 |
Family
ID=4342689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH861765A CH449631A (de) | 1965-06-21 | 1965-06-21 | Verfahren zur Herstellung von 1,2,5-Imidazolderivaten |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH449631A (enrdf_load_stackoverflow) |
| DK (1) | DK107099C (enrdf_load_stackoverflow) |
| IS (1) | IS689B6 (enrdf_load_stackoverflow) |
| NL (1) | NL6608513A (enrdf_load_stackoverflow) |
| NO (1) | NO117030B (enrdf_load_stackoverflow) |
| SE (1) | SE328297B (enrdf_load_stackoverflow) |
-
1965
- 1965-06-21 CH CH861765A patent/CH449631A/de unknown
- 1965-07-24 DK DK382965A patent/DK107099C/da active
-
1966
- 1966-06-20 IS IS1568A patent/IS689B6/is unknown
- 1966-06-20 NL NL6608513A patent/NL6608513A/xx unknown
- 1966-06-20 NO NO16355766A patent/NO117030B/no unknown
- 1966-06-21 SE SE843866A patent/SE328297B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IS1568A7 (is) | 1966-12-22 |
| DK107099C (da) | 1967-04-24 |
| IS689B6 (is) | 1969-11-10 |
| SE328297B (enrdf_load_stackoverflow) | 1970-09-14 |
| NO117030B (enrdf_load_stackoverflow) | 1969-06-23 |
| NL6608513A (enrdf_load_stackoverflow) | 1966-12-22 |
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