DE2107405A1 - Verfahren zur Herstellung von 5 Nitro lmidazoldenvaten - Google Patents
Verfahren zur Herstellung von 5 Nitro lmidazoldenvatenInfo
- Publication number
- DE2107405A1 DE2107405A1 DE19712107405 DE2107405A DE2107405A1 DE 2107405 A1 DE2107405 A1 DE 2107405A1 DE 19712107405 DE19712107405 DE 19712107405 DE 2107405 A DE2107405 A DE 2107405A DE 2107405 A1 DE2107405 A1 DE 2107405A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- carbon atoms
- preparation
- nitroimidazole
- nitro
- 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 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 6
- 150000004958 5-nitroimidazoles Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VUFBCWUJICCKDU-UHFFFAOYSA-N 1-(2-methylimidazol-1-yl)propan-2-ol Chemical compound CC(O)CN1C=CN=C1C VUFBCWUJICCKDU-UHFFFAOYSA-N 0.000 description 3
- IRLDHIQLUDFMFY-UHFFFAOYSA-N 1-(2-methylimidazol-1-yl)propan-2-yl acetate Chemical compound CC(=O)OC(C)CN1C=CN=C1C IRLDHIQLUDFMFY-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- OLYYLDXLNQMUJM-UHFFFAOYSA-N CC(=O)OC(C)CN1C(C)=NC=C1[N+]([O-])=O Chemical compound CC(=O)OC(C)CN1C(C)=NC=C1[N+]([O-])=O OLYYLDXLNQMUJM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 alkanoyl chloride Chemical compound 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KPQZUUQMTUIKBP-UHFFFAOYSA-N 1-(2-methyl-5-nitro-1-imidazolyl)-2-propanol Chemical compound CC(O)CN1C(C)=NC=C1[N+]([O-])=O KPQZUUQMTUIKBP-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- 150000004960 4-nitroimidazoles Chemical group 0.000 description 1
- KGIMLHQWXCGWKF-UHFFFAOYSA-N C(C)(=O)OC(CN1C(=NC(=C1)[N+](=O)[O-])C)C Chemical compound C(C)(=O)OC(CN1C(=NC(=C1)[N+](=O)[O-])C)C KGIMLHQWXCGWKF-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940124323 amoebicide Drugs 0.000 description 1
- 239000000059 antiamebic agent Substances 0.000 description 1
- 239000003904 antiprotozoal agent Substances 0.000 description 1
- 239000003716 antitrichomonal agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide 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
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7005444A FR2079880A5 (enExample) | 1970-02-16 | 1970-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2107405A1 true DE2107405A1 (de) | 1971-09-02 |
Family
ID=9050726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712107405 Pending DE2107405A1 (de) | 1970-02-16 | 1971-02-16 | Verfahren zur Herstellung von 5 Nitro lmidazoldenvaten |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4980066A (enExample) |
| BE (1) | BE762991A (enExample) |
| CA (1) | CA920604A (enExample) |
| CH (1) | CH513178A (enExample) |
| DE (1) | DE2107405A1 (enExample) |
| FR (1) | FR2079880A5 (enExample) |
| GB (1) | GB1278757A (enExample) |
| IL (1) | IL36193A0 (enExample) |
| NL (1) | NL7101642A (enExample) |
| OA (1) | OA03569A (enExample) |
| YU (1) | YU36671A (enExample) |
| ZA (1) | ZA71917B (enExample) |
-
1970
- 1970-02-16 FR FR7005444A patent/FR2079880A5/fr not_active Expired
-
1971
- 1971-02-06 OA OA54166A patent/OA03569A/xx unknown
- 1971-02-08 NL NL7101642A patent/NL7101642A/xx unknown
- 1971-02-15 CH CH215371A patent/CH513178A/fr not_active IP Right Cessation
- 1971-02-15 JP JP46006732A patent/JPS4980066A/ja active Pending
- 1971-02-15 CA CA105410A patent/CA920604A/en not_active Expired
- 1971-02-15 BE BE762991A patent/BE762991A/xx unknown
- 1971-02-15 ZA ZA710917A patent/ZA71917B/xx unknown
- 1971-02-15 IL IL36193A patent/IL36193A0/xx unknown
- 1971-02-16 YU YU00366/71A patent/YU36671A/xx unknown
- 1971-02-16 DE DE19712107405 patent/DE2107405A1/de active Pending
- 1971-04-19 GB GB21739/71A patent/GB1278757A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| YU36671A (en) | 1976-12-31 |
| NL7101642A (enExample) | 1971-08-18 |
| CH513178A (fr) | 1971-09-30 |
| OA03569A (fr) | 1971-03-30 |
| ZA71917B (en) | 1972-06-28 |
| JPS4980066A (enExample) | 1974-08-02 |
| FR2079880A5 (enExample) | 1971-11-12 |
| CA920604A (en) | 1973-02-06 |
| IL36193A0 (en) | 1971-04-28 |
| GB1278757A (en) | 1972-06-21 |
| BE762991A (fr) | 1971-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |