DE2414280C2 - Verfahren zur Herstellung von 1-Methyl-5-nitroimidazolen - Google Patents
Verfahren zur Herstellung von 1-Methyl-5-nitroimidazolenInfo
- Publication number
- DE2414280C2 DE2414280C2 DE2414280A DE2414280A DE2414280C2 DE 2414280 C2 DE2414280 C2 DE 2414280C2 DE 2414280 A DE2414280 A DE 2414280A DE 2414280 A DE2414280 A DE 2414280A DE 2414280 C2 DE2414280 C2 DE 2414280C2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- nitroimidazole
- methyl
- water
- formic acid
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 6
- JLZXSFPSJJMRIX-UHFFFAOYSA-N 1-methyl-5-nitroimidazole Chemical class CN1C=NC=C1[N+]([O-])=O JLZXSFPSJJMRIX-UHFFFAOYSA-N 0.000 title description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 36
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 18
- 235000019253 formic acid Nutrition 0.000 description 18
- 239000007858 starting material Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 description 12
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VYDWQPKRHOGLPA-UHFFFAOYSA-N 5-nitroimidazole Chemical group [O-][N+](=O)C1=CN=CN1 VYDWQPKRHOGLPA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 150000004958 5-nitroimidazoles Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 5
- SQZCZXRYOJJCDU-UHFFFAOYSA-N 5-nitro-2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=C([N+]([O-])=O)N1 SQZCZXRYOJJCDU-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- -1 2-ethyl- Chemical group 0.000 description 2
- WSYOWIMKNNMEMZ-UHFFFAOYSA-N 5-methyl-4-nitro-1h-imidazole Chemical compound CC=1NC=NC=1[N+]([O-])=O WSYOWIMKNNMEMZ-UHFFFAOYSA-N 0.000 description 2
- KKEBJZZNQLGYJE-UHFFFAOYSA-N 5-nitro-2-octyl-1h-imidazole Chemical compound CCCCCCCCC1=NC=C([N+]([O-])=O)N1 KKEBJZZNQLGYJE-UHFFFAOYSA-N 0.000 description 2
- 208000000230 African Trypanosomiasis Diseases 0.000 description 2
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FEGUTYIXCZDKJV-UHFFFAOYSA-N 1,4-dimethyl-5-nitroimidazole Chemical compound CC=1N=CN(C)C=1[N+]([O-])=O FEGUTYIXCZDKJV-UHFFFAOYSA-N 0.000 description 1
- UKAXKCXOBZGQAK-UHFFFAOYSA-N 2,5-dimethyl-4-nitro-1h-imidazole Chemical compound CC1=NC([N+]([O-])=O)=C(C)N1 UKAXKCXOBZGQAK-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- IWYVYUZADLIDEY-UHFFFAOYSA-N 4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1 IWYVYUZADLIDEY-UHFFFAOYSA-N 0.000 description 1
- 206010001986 Amoebic dysentery Diseases 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 241000223782 Ciliophora Species 0.000 description 1
- 208000009514 Dourine Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NTAFJUSDNOSFFY-UHFFFAOYSA-N Ipronidazole Chemical compound CC(C)C1=NC=C([N+]([O-])=O)N1C NTAFJUSDNOSFFY-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000223105 Trypanosoma brucei Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 201000001505 hemoglobinuria Diseases 0.000 description 1
- 208000029080 human African trypanosomiasis Diseases 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
- 239000002917 insecticide Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 201000002612 sleeping sickness Diseases 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2414280A DE2414280C2 (de) | 1974-03-25 | 1974-03-25 | Verfahren zur Herstellung von 1-Methyl-5-nitroimidazolen |
| US05/557,270 US4021442A (en) | 1974-03-25 | 1975-03-11 | Production of 1-alkyl-5-nitroimidazoles |
| NLAANVRAGE7503352,A NL184618C (nl) | 1974-03-25 | 1975-03-20 | Werkwijze voor het bereiden van 1-alkyl-5-nitro-imidazolen. |
| FR7509065A FR2265743B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-25 | 1975-03-24 | |
| GB12080/75A GB1493496A (en) | 1974-03-25 | 1975-03-24 | Production of 1-alkyl-5-nitroimidazoles |
| JP50035018A JPS50130762A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-25 | 1975-03-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2414280A DE2414280C2 (de) | 1974-03-25 | 1974-03-25 | Verfahren zur Herstellung von 1-Methyl-5-nitroimidazolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2414280A1 DE2414280A1 (de) | 1975-10-23 |
| DE2414280C2 true DE2414280C2 (de) | 1981-12-17 |
Family
ID=5911073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2414280A Expired DE2414280C2 (de) | 1974-03-25 | 1974-03-25 | Verfahren zur Herstellung von 1-Methyl-5-nitroimidazolen |
Country Status (6)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3026846A1 (de) * | 1980-07-16 | 1982-02-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,2-dimethyl-5-nitroimidazol |
| DE3132025A1 (de) * | 1981-08-13 | 1983-03-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von 1,2-dimethyl-5-nitroimidazol von hoher reinheit |
| EP0126183A1 (de) * | 1982-12-23 | 1984-11-28 | A. Nattermann & Cie. GmbH | Substituierte 5(4)-Nitroimidazole sowie Verfahren zu ihrer Herstellung |
| FR2625997B1 (fr) * | 1988-01-15 | 1990-06-08 | Rhone Poulenc Sante | Procede de preparation du dimethyl-1,2 nitro-5 imidazole |
| CN1023221C (zh) * | 1988-01-15 | 1993-12-22 | 罗纳·布朗克制药公司 | 1-烷基-5-硝基咪唑的制备方法 |
| UA80839C2 (en) * | 2002-10-15 | 2007-11-12 | 1-substituted 4-nitroimidazole compound and process for producing the same | |
| MY145079A (en) * | 2002-10-15 | 2011-12-15 | Otsuka Pharma Co Ltd | 1-substituted-4-nitroimidazole compound and method for preparing the same |
| TWI300409B (en) * | 2004-02-18 | 2008-09-01 | Otsuka Pharma Co Ltd | Method for producing 4-nitroimidazole compound |
| RU2528025C1 (ru) * | 2013-03-29 | 2014-09-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Национальный исследовательский Томский государственный университет" (ТГУ) | Способ получения диметридазола |
| EP3010345A4 (en) * | 2013-06-21 | 2017-04-12 | The Regents of The University of California | Expanded therapeutic potential in nitroheteroaryl antimicrobials |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3399211A (en) * | 1964-03-10 | 1968-08-27 | Merck & Co Inc | Production of 2-aryl-4(5)-nitroimidazoles |
| CA922319A (en) * | 1964-10-26 | 1973-03-06 | Pfizer Limited | Process of preparing 5-nitroimidazole derivatives |
| AT268273B (de) * | 1966-05-07 | 1969-02-10 | Krka Tovarna Zdravil | Verfahren zur Herstellung von neuen 5-Nitroimidazoläthern |
| NL7017486A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-12-15 | 1971-06-17 |
-
1974
- 1974-03-25 DE DE2414280A patent/DE2414280C2/de not_active Expired
-
1975
- 1975-03-11 US US05/557,270 patent/US4021442A/en not_active Expired - Lifetime
- 1975-03-20 NL NLAANVRAGE7503352,A patent/NL184618C/xx not_active IP Right Cessation
- 1975-03-24 GB GB12080/75A patent/GB1493496A/en not_active Expired
- 1975-03-24 FR FR7509065A patent/FR2265743B1/fr not_active Expired
- 1975-03-25 JP JP50035018A patent/JPS50130762A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL184618C (nl) | 1989-09-18 |
| GB1493496A (en) | 1977-11-30 |
| DE2414280A1 (de) | 1975-10-23 |
| FR2265743A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-24 |
| FR2265743B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-23 |
| US4021442A (en) | 1977-05-03 |
| NL184618B (nl) | 1989-04-17 |
| JPS50130762A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-16 |
| NL7503352A (nl) | 1975-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination |