CH204745A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. - Google Patents
Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.Info
- Publication number
- CH204745A CH204745A CH204745DA CH204745A CH 204745 A CH204745 A CH 204745A CH 204745D A CH204745D A CH 204745DA CH 204745 A CH204745 A CH 204745A
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydride
- imidazole
- ether
- substituted
- preparation
- Prior art date
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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Verfahren zur Darstellung eines in 2-Stellung substituierten Imidazoldihydrids-(4,5). Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines in 2-Stellung substituierten Imidazol-dihydrids- (4,5), welches dadurch gekennzeichnet ist, dass man einen 1-Naphtoxyacetiminoäther mit Äthylendiamin umsetzt.
Das so gewonnene 2-(1'-Naphtoxymethyl)- imidazol-dihydrid-(4,5) bildet ein farbloses Hydrochlorid vom F. 235 bis 237 .
Die neue Verbindung kann als Arznei mittel verwendet werden.
<I>Beispiel:</I> 26,5 Teile 1-Naphtoxyacetiminoäthyl- äther-hydrochlorid der Formel
EMI0001.0013
(hergestellt aus dem beim Erhitzen von a- Naphtol mit Chloracetonitril in Acetonlösung und Gegenwart von Pottasche entstehenden 1-Naphtoxyacetonitril, Kpo,r, 140 bis 143'; F. 65 ), aus dem sich während der Umset zung 1-Naphtoxyacetiminoäthyläther bildet, werden in absolutem Alkohol gelöst.
Man fügt ziemlich rasch 6 Teile Äthylendiamin hinzu, erhitzt langsam auf<B>100'</B> und hält einige Stunden bei dieser Temperatur. Her nach vertreibt man den Alkohol, versetzt den Rückstand mit Natronlauge und extrahiert erschöpfend mit Benzol. Nach dem Trocknen über Pottasche und nachherigem Vertreiben des Benzols bleibt das 2-(1'-Naphtoxy- methyl)-imidazoldihydrid-(4,5) der Formel
EMI0001.0028
zurück. An Stelle von 1-Naphtoxyacetiminoäthyl- äther kann ebensogut ein anderer Äther, wie z.
B. der Methyl-, Propyl- oder Butyläther Verwendung finden. Statt vom salzsauren Salz des 1-Na.pht- oayacetiminoäthers kann man auch von einem andern Salze, wie z. B. vom brom- wa.sserstoffsauren, vom schwefelsauren oder vom methylschwefelsauren Salz ausgehen.
Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. The subject of the present patent is a process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, which is characterized in that a 1-naphthoxyacetimino ether is reacted with ethylenediamine.
The 2- (1'-naphtoxymethyl) - imidazole-dihydride- (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 235 to 237.
The new compound can be used as a medicine.
<I> Example: </I> 26.5 parts of 1-naphtoxyacetiminoethyl ether hydrochloride of the formula
EMI0001.0013
(made from the 1-naphtoxyacetonitrile, Kpo, r, 140 to 143 '; F. 65) which is formed when a-naphthol is heated with chloroacetonitrile in acetone solution and the presence of potash, from which 1-naphtoxyacetiminoethyl ether is formed during the reaction dissolved in absolute alcohol.
6 parts of ethylenediamine are added fairly quickly, heated slowly to <B> 100 '</B> and held at this temperature for a few hours. The alcohol is then driven off, the residue is mixed with sodium hydroxide solution and extracted exhaustively with benzene. After drying over potash and then driving off the benzene, the 2- (1'-naphthoxymethyl) imidazole dihydride (4,5) of the formula remains
EMI0001.0028
back. Instead of 1-Naphtoxyacetiminoäthyl- ether, another ether, such as z.
B. the methyl, propyl or butyl ethers are used. Instead of the hydrochloric acid salt of 1-Na.pht- oayacetiminoäthers one can also use another salt, such as z. B. from the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH204745T | 1935-07-23 | ||
CH199906T | 1938-09-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH204745A true CH204745A (en) | 1939-05-15 |
Family
ID=25723398
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH204745D CH204745A (en) | 1935-07-23 | 1935-07-23 | Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH204745A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3277112A (en) * | 1963-09-20 | 1966-10-04 | Ciba Geigy Corp | Phenoxy 2-(1, 3-diaza-2-cycloalkenyl)compounds |
-
1935
- 1935-07-23 CH CH204745D patent/CH204745A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3277112A (en) * | 1963-09-20 | 1966-10-04 | Ciba Geigy Corp | Phenoxy 2-(1, 3-diaza-2-cycloalkenyl)compounds |
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