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WO1991009022A1 - Oxydes de 2,2-dialkyle-2h-imidazole-1 et leur procede d'obtention - Google Patents

Oxydes de 2,2-dialkyle-2h-imidazole-1 et leur procede d'obtention Download PDF

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Publication number
WO1991009022A1
WO1991009022A1 PCT/SU1989/000311 SU8900311W WO9109022A1 WO 1991009022 A1 WO1991009022 A1 WO 1991009022A1 SU 8900311 W SU8900311 W SU 8900311W WO 9109022 A1 WO9109022 A1 WO 9109022A1
Authority
WO
WIPO (PCT)
Prior art keywords
imidazole
sect
oxides
dialkyl
general formula
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.)
Ceased
Application number
PCT/SU1989/000311
Other languages
English (en)
Russian (ru)
Inventor
Igor Anatolievich Kiriljuk
Igor Alexeevich Grigoriev
Leonid Borisovich Volodarsky
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia
Original Assignee
Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia filed Critical Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia
Priority to PCT/SU1989/000311 priority Critical patent/WO1991009022A1/fr
Publication of WO1991009022A1 publication Critical patent/WO1991009022A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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

Definitions

  • the indicated compounds may be used for stable imidazole radicals and, in addition to this, are used for improper use.
  • the stable impaired radicals of imidazoline are variable in terms of inhibitory measures, such as antidepressants, anti-oxidants, and radioactive sensitizers.
  • 3-imidazoline-3-oxides 3-imidazolines, which are deficient and are stable and are stable compounds of stable imitazole radicals, are imidazoline.
  • the inventive compounds provide colorless liquids or crystalline materials with a melting point up to 220 ° ⁇ , which are resistant to refrigeration.
  • the compound construction is proved by the data of ⁇ , ⁇ , ⁇ -spectroscopy and elemental analysis.
  • the disclosure of the invention involves the preparation of 2,2-dialkyl-2 ⁇ -imidazole- ⁇ -oxides, which means that there is an agreement on the availability of a car
  • the obtained temperature of the process is optimal, since the reaction below the temperature of 20 ° 0 leads to a significant increase in the time of the reaction. Raising the temperature above ⁇ 00 ° 0 leads to a strong refinement of the reactive mass, which makes it difficult to isolate the target products and reduce output.
  • the product is minimized - 5 -
  • the claimed compounds contain different functional groups, which determine the complex connection with metal ions. This makes it possible to use a large number of 10 to call for original reagents to produce stable, high-imidazole impairment.
  • Hydroxymethymethylketone mixes with an excess of aliphas 35 tic ketone, acetate, ammonia and acetic acid. The mixture is boiled in a water bath ' with a refrigerator. The resulting reactive mass is diluted with water in 5-10 times ⁇ ⁇ 91/09022
  • the extract is dried, after which the solvent is evaporated.
  • the resulting product is cleaned, for example, by using method 5, processing, installation, or freezing.
  • the extract dries Mg50, the ethyl acetate is evaporated, the treated mass is sprayed with 50 ml of heptane and is evaporated again.
  • the waste is dissolved with 20 ml of a mixture of ethyl acetate -
  • Hexane 1 1. Received 0.8 g of 2-methyl-4-phenyl-2-chloro-methyl-2 ⁇ -imidazole- ⁇ -oxide, yield (53 $), ⁇ . ⁇ l. ⁇ 40- ⁇ 42 ° ⁇ . - II -
  • the active mass is poured into 300 ml of water and is extracted with 5 times 70 ml of water.
  • the extract is rinsed off with a saturated solution of 2 ⁇ 0 ⁇ , it is dried immediately, it is freezed, it is freezed out at a temperature - thirteen -
  • Source ⁇ - radicals exceeded the compound ⁇ ' (acac) 2 (0 2 ⁇ réelle 2 ⁇ ) ⁇ committee7 When this complex is repaired in benzene (0.05 • ) is installed
  • 2,2-dialkyl-2 ⁇ -imidazole- ⁇ -oxides may be used in chemistry - for the production of nitrous radicals of imidazole ; At the same time, it may be necessary to catch and register live substances in the atmosphere of industrial and industrial applications.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Nouvelles compositions: oxydes de 2,2-dialkyle-2H-imidazole-1 ayant la formule générale (I), dans laquelle R1 = C6H5, CH3, CH=NOH, p-O2NC6H4, M-O2NC6H4; R2 = CH3, CH2CH2CH3; R3 = CH3, (CH2)7CH3, CH2COOC2H5, CH2CH2COOH3, CH2CH2COOH, CH2CH2CH3, (CH2)8CH3. Le procédé d'obtention desdites compositions consiste en ce que les hydroximinométhylcétones de la formule générale (II) (dans laquelle R1 = C6H5, CH3, CH=NOH, p-O2NC6H4, M-O2NC6H4) sont mises en interaction avec des cétones aliphatiques de la formule: R2-CO-R3 (dans laquelle R2 = CH3, CH2CH2CH3; R3 = CH3, (CH2)7CH3, CH2COOC2H5, CH2CH2COOCH3, CH2CH2COOH, CH2CH2CH3, (CH2)8CH3) et avec de l'acétate d'ammonium. Le rapport molaire des composants est 1:3,5 à 20:1,6 à 6,0, respectivement. Le procédé est mis en ÷uvre dans le milieu d'acide acétique à une température comprise entre 20 et 100 °C. On obtient, en résultat, une masse de réaction contenant le produit désiré, lequel est ensuite extrait.
PCT/SU1989/000311 1989-12-12 1989-12-12 Oxydes de 2,2-dialkyle-2h-imidazole-1 et leur procede d'obtention Ceased WO1991009022A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/SU1989/000311 WO1991009022A1 (fr) 1989-12-12 1989-12-12 Oxydes de 2,2-dialkyle-2h-imidazole-1 et leur procede d'obtention

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/SU1989/000311 WO1991009022A1 (fr) 1989-12-12 1989-12-12 Oxydes de 2,2-dialkyle-2h-imidazole-1 et leur procede d'obtention

Publications (1)

Publication Number Publication Date
WO1991009022A1 true WO1991009022A1 (fr) 1991-06-27

Family

ID=21617606

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SU1989/000311 Ceased WO1991009022A1 (fr) 1989-12-12 1989-12-12 Oxydes de 2,2-dialkyle-2h-imidazole-1 et leur procede d'obtention

Country Status (1)

Country Link
WO (1) WO1991009022A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU389097A1 (ru) * 1971-05-03 1973-07-05 Новосибирский Институт органической химии Сибирского отделени СССР Способ получения
SU420627A1 (ru) * 1971-05-03 1974-03-25 Л. Б. Володарский , Т. К. Севасть нова Способ получения производных 2,2,5,5- тетразамещенных з-имидазолин-1-оксилов
US3927019A (en) * 1971-02-22 1975-12-16 Synvar Ass 1-Oxylimidazolinyl compounds used as stable free radical pH indicators
SU579272A1 (ru) * 1975-12-16 1977-11-05 Новосибирский институт органической химии СО АН СССР Производные 2,2,5,5-тетраалкил-3-имидазолин3-оксида, как исходные соединени дл синтеза стабильных радикалов, и способ их получени
US4328349A (en) * 1980-10-08 1982-05-04 Sk&F Lab Co. Process for preparing 5-methyl-4-imidazolecarboxylic acid esters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927019A (en) * 1971-02-22 1975-12-16 Synvar Ass 1-Oxylimidazolinyl compounds used as stable free radical pH indicators
SU389097A1 (ru) * 1971-05-03 1973-07-05 Новосибирский Институт органической химии Сибирского отделени СССР Способ получения
SU420627A1 (ru) * 1971-05-03 1974-03-25 Л. Б. Володарский , Т. К. Севасть нова Способ получения производных 2,2,5,5- тетразамещенных з-имидазолин-1-оксилов
SU579272A1 (ru) * 1975-12-16 1977-11-05 Новосибирский институт органической химии СО АН СССР Производные 2,2,5,5-тетраалкил-3-имидазолин3-оксида, как исходные соединени дл синтеза стабильных радикалов, и способ их получени
US4328349A (en) * 1980-10-08 1982-05-04 Sk&F Lab Co. Process for preparing 5-methyl-4-imidazolecarboxylic acid esters

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