GB796996A - Imidazole derivatives - Google Patents
Imidazole derivativesInfo
- Publication number
- GB796996A GB796996A GB23873/56A GB2387356A GB796996A GB 796996 A GB796996 A GB 796996A GB 23873/56 A GB23873/56 A GB 23873/56A GB 2387356 A GB2387356 A GB 2387356A GB 796996 A GB796996 A GB 796996A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- imidaz
- tetrahydro
- hydroxyethyl
- imidazole
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The invention comprises the 1-substituted-2,3,5,6 - tetrahydro - 1 - imidaz - (1,2-a) - imidazoles of the formula <FORM:0796996/IV (b)/1> in which R is an alkyl radical having from 1 to 20 carbon atoms, an aralkyl radical or a dialkylaminoalkyl radical in which the alkyl groups each contain 1-4 carbon atoms, and their acid salts. They may be prepared by refluxing a 1 - (b - hydroxyethyl) - 2 - substituted - amino-2-imidazoline of formula <FORM:0796996/IV (b)/2> with thionyl chloride and refluxing the 1-(b -chloroethyl) - 2 - substituted - amino - imidazolinium chloride so formed with an alcoholic solution of an alkali metal hydroxide. In the examples: (a) a solution of thionyl chloride in chloroform is added to 1-(b -hydroxyethyl)-2-(g -dimethylaminopropylamino) - 2 - imidazoline in chloroform solution and the mixture is refluxed, the chloroform and excess thionyl chloride are removed and the residue is dissolved in methanol and treated with potassium hydroxide dissolved in potassium hydroxide to give 1-(g -dimethylaminopropyl) - 2,3,5,6 - tetrahydro - 1 - imidaz(1,2-a) - imidazole; (b) the process of (a) is repeated using 1 - (b - hydroxyethyl) - 2 - (g -diethylaminopropylamino) - 2 - imidazoline as starting material and methanolic sodium hydroxide in the second stage to give 1-(g - diethylaminopropyl) - 2,3,5,6 - tetrahydro - 1 - imidaz(1,2-a)-imidazole; (c) thionyl chloride is refluxed with 1 - (b - hydroxyethyl - 1 - 2 - benzylamino-2-imidazolinium chloride to give 1-(b -chloroethyl) - 2 - benzylamino - 2 - imidazoline which is refluxed with methanolic potassium hydroxide to give 1-benzyl-2,3,5,6-tetrahydro-1-imidaz-(1,2-a) - imidazole; (d) 1 - (b - hydroxyethyl)-2-(b - dimethylaminoethylamino) - 2 - imidazoline is converted to its hydrochloride salt which is refluxed with alcoholic potassium hydroxide to give 1 - (b - dimethylaminoethyl) - 2,3,5,6-tetrahydro - 1 - imidaz - (1,2-a) - imidazole; (e) 1-(b - hydroxyethyl) - 2 - (b - diethylaminoethylamino) - 2 - imidazoline hydrochloride is refluxed with thionyl chloride to give 1-(b -chloroethyl) - 2 - (b - diethylaminoethylamino) - 2 - imidazoline hydrochloride which is refluxed with alcoholic potash to give 1-(b -diethylaminoethyl)-2,3,5,6 - tetrahydro - 1 - imidaz - (1,2,-a) - imidazole; (f) 1 - (b - hydroxyethyl) - 2 - (b - phenylethyl) - 2 - imidazolinium chloride is refluxed with thionyl chloride and the product is refluxed with alcoholic potash to give 1-(b -phenylethyl)-2,3,5,6 - tetrahydro - 1 - imidaz - (1,2-a) - imidazole; (g) 1 - (b - hydroxyethyl) - 2 - n - propyl - amino - 2 - imidazolinium chloride is heated by the process of (f) to give 1-n-propyl-2,3,5,6-tetrahydro - 1 - imidaz - (1,2-a) - imidazole; (h) 1 - (b - hydroxyethyl) - 2 - n - octylamino - 2 - imidazolinium chloride is treated by the process of (f) to give 1-n-octyl-2,3,5,6-tetrahydro-1-imidaz - (1,2-a) - imidazole; (j) 1 - (b - hydroxyethyl) - 2 - n - dodecylamino - 2 - imidazolinium chloride is treated by the process of (f) to give 1 - n - dodecyl - 2,3,5,6 - tetrahydro - 1 - imidaz - (1,2-a) - imidazole; (k) 1 - (b - hydroxyethyl)-2-n - tetradecylamino - 2 - imidazoline is treated by the process of (f) to give 1-n-tetradecyl-2,3,5,6 - tetrahydro - 1 - imidaz - (1,2-a) - imidazole; (1) 1 - (b - hydroxyethyl) - 2 - (n - hexadecylamino) - 2 - imidazoline is treated by the process of (f) to give 1-n-hexadecyl-2,3,5,6-tetrahydro - 1 - imidaz - (1,2-a) - imidazole; and (m) 1 - (b - hydroxyethyl) - 2 - (n - octadecylamino)-2-imidazoline is treated by the process of (f) to give 1 - n - octadecyl - 2,3,5,6 - tetrahydro - 1 - imidaz-(1,2-a)-imidazole. Specification 796,997 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US796996XA | 1956-03-29 | 1956-03-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB796996A true GB796996A (en) | 1958-06-25 |
Family
ID=22152219
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23873/56A Expired GB796996A (en) | 1956-03-29 | 1956-08-02 | Imidazole derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB796996A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3865836A (en) * | 1972-12-08 | 1975-02-11 | Janssen Pharmaceutica Nv | Bicyclic imidazoles |
US3923808A (en) * | 1972-12-08 | 1975-12-02 | Janssen Pharmaceutica Nv | Bicyclic imidazoles and pyrimidines |
US3925383A (en) * | 1972-12-08 | 1975-12-09 | Janssen Pharmaceutica Nv | Bicyclic imidazoles and pyrimidines |
US3983133A (en) * | 1974-08-13 | 1976-09-28 | Janssen Pharmaceutica N.V. | 2-Substituted imidazolines |
WO1992004385A1 (en) * | 1990-09-06 | 1992-03-19 | The British Petroleum Company Plc | Fuels and fuel additives |
-
1956
- 1956-08-02 GB GB23873/56A patent/GB796996A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3865836A (en) * | 1972-12-08 | 1975-02-11 | Janssen Pharmaceutica Nv | Bicyclic imidazoles |
US3923808A (en) * | 1972-12-08 | 1975-12-02 | Janssen Pharmaceutica Nv | Bicyclic imidazoles and pyrimidines |
US3925383A (en) * | 1972-12-08 | 1975-12-09 | Janssen Pharmaceutica Nv | Bicyclic imidazoles and pyrimidines |
US3983133A (en) * | 1974-08-13 | 1976-09-28 | Janssen Pharmaceutica N.V. | 2-Substituted imidazolines |
WO1992004385A1 (en) * | 1990-09-06 | 1992-03-19 | The British Petroleum Company Plc | Fuels and fuel additives |
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