DE606615C - Process for the preparation of tetrazole pellets of the terpene series - Google Patents
Process for the preparation of tetrazole pellets of the terpene seriesInfo
- Publication number
- DE606615C DE606615C DEK130899D DEK0130899D DE606615C DE 606615 C DE606615 C DE 606615C DE K130899 D DEK130899 D DE K130899D DE K0130899 D DEK0130899 D DE K0130899D DE 606615 C DE606615 C DE 606615C
- Authority
- DE
- Germany
- Prior art keywords
- tetrazole
- camphor
- pellets
- preparation
- benzene
- 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
- 150000003536 tetrazoles Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 2
- 150000003505 terpenes Chemical class 0.000 title description 2
- 235000007586 terpenes Nutrition 0.000 title description 2
- 239000008188 pellet Substances 0.000 title 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 12
- 241000723346 Cinnamomum camphora Species 0.000 claims description 11
- 229930008380 camphor Natural products 0.000 claims description 10
- 229960000846 camphor Drugs 0.000 claims description 10
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 6
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- USMNOWBWPHYOEA-UHFFFAOYSA-N 3‐isothujone Chemical compound CC1C(=O)CC2(C(C)C)C1C2 USMNOWBWPHYOEA-UHFFFAOYSA-N 0.000 description 7
- 229930007110 thujone Natural products 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- -1 oxime esters Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229930007107 (+)-beta-thujone Natural products 0.000 description 1
- USMNOWBWPHYOEA-XKSSXDPKSA-N (+)-beta-thujone Chemical compound O=C([C@H]1C)C[C@@]2(C(C)C)[C@@H]1C2 USMNOWBWPHYOEA-XKSSXDPKSA-N 0.000 description 1
- 229930007105 (-)-alpha-thujone Natural products 0.000 description 1
- ZKZMIYKCFLBKLV-UHFFFAOYSA-N 1,2,2-trimethylcyclopentane-1,3-dicarbonitrile Chemical compound CC1(C)C(C#N)CCC1(C)C#N ZKZMIYKCFLBKLV-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NNVLMKVCBJABNY-UHFFFAOYSA-N N1N=NN=C1.C12(C(=O)CC(CC1)C2(C)C)C Chemical compound N1N=NN=C1.C12(C(=O)CC(CC1)C2(C)C)C NNVLMKVCBJABNY-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 229930007108 beta-thujone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- YMICGVDWLKMEHM-UHFFFAOYSA-N hydrazoic acid benzene Chemical compound N=[N+]=[N-].C1=CC=CC=C1 YMICGVDWLKMEHM-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940085790 synthetic camphor Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- USMNOWBWPHYOEA-MRTMQBJTSA-N α-thujone Chemical compound O=C([C@@H]1C)C[C@@]2(C(C)C)[C@@H]1C2 USMNOWBWPHYOEA-MRTMQBJTSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Tetrazolabkömmlingen der Terpenreihe Aus den Patentschriften 439 041, K1. 12p, und 455 585, K1. i2,0, sind Verfahren bekannt, nach welchen man durch Behandlung von Carbonylverbindungen mit Stickstoffwasserstoffsäure in Gegenwart von Katalysatoren allgemein zu Tetrazolen gelangt.Process for the preparation of tetrazole derivatives of the terpene series From patent specifications 439 041, K1. 12p, and 455 585, K1. i2,0, are procedures known, after which one by treating carbonyl compounds with hydrazoic acid generally leads to tetrazoles in the presence of catalysts.
Andererseits können die gleichen Tetrazole aus den entsprechenden Carbonylverbindungen auch nach dem Verfahren der Patentschrift 538 984 K1. 12p, in der Weise gewonnen werden, daß letztere mit Hydroxylamin zu den Oximen umgesetzt, diese in die Oximester aromatischer Sulfonsäuren - übergeführt und dann in Gegenwart von Stickstoffwasserstoffsäure oder Aziden der Beckmannschen Umlagerung unterworfen werden.On the other hand, the same tetrazoles from the corresponding Carbonyl compounds also according to the method of patent specification 538 984 K1. 12p, are obtained in such a way that the latter is reacted with hydroxylamine to form the oximes, these are converted into the oxime esters of aromatic sulfonic acids - and then in the presence subjected to the Beckmann rearrangement by hydrazoic acid or azides will.
Es wurde nun gefunden, daß man, ausgehend vom Kampfer oder Thujon, nach diesen Verfahren Tetrazole der Formel Clo 1116 N4 erhält. Diese neuen Stoffe sind therapeutisch mit Vorteil anwendbar. Sie enthalten gleichzeitig die Atomgruppierung des Kampfers bzw. Thujons und die des Pentamethylentetrazols, alles Stoffe, denen analeptische Wirkung innewohnt. Dementsprechend sind die durch die Vereinigung der beiden Ringsysteme entstandenen Körper in gleichem Sinne, aber stärker und länger anhaltend wirksam als das Pentamethylentetrazol. Vom Kampfer unterscheiden sich beide, insbesondere aber das vom Kampfer abgeleitete Tetrazol, durch das Fehlen lähmender Eigenschaften und durch die erheblich größere Löslichkeit in Wasser.It has now been found that, proceeding from camphor or thujone, obtained by this process tetrazoles of the formula Clo 1116 N4. These new fabrics are therapeutically applicable with advantage. They also contain the atom grouping of camphor or thujone and that of pentamethylenetetrazole, all substances to which intrinsic analeptic effect. Accordingly, by the union of the Both ring systems created bodies in the same sense, but stronger and longer lastingly effective than pentamethylenetetrazole. Different from camphor both, but especially the camphor-derived tetrazole, due to the lack of it paralyzing properties and the considerably greater solubility in water.
Ausgehend vom synthetischen Kampfer erhält man ein inaktives Produkt. Dagegen drehen die aus den optisch aktiven Formen hergestellten Produkte die Ebene des polarisierten Lichts. Z. B. dreht das aus natürlichem rechtsdrehendem Kampfer hergestellte Tetrazol die Ebene des polarisierten Lichts nach links.Starting from the synthetic camphor you get an inactive product. In contrast, the products made from the optically active shapes rotate the plane of polarized light. E.g. this turns from natural right hand camphor made tetrazole left the plane of polarized light.
Unterschiede in der Wirkung der optisch aktiven und der razemischen Verbindungen sind wie beim Kampfer nicht feststellbar: Das gleiche gilt für die lediglich durch den Schmelzpunkt verschiedenen Produkte, welche aus Thujon des Handels oder aus reinem ß= Thu j an gewonnen werden. Beispiel i In eine Lösung von 30,4 g (o,2 Mol) Kampfer in 25o ccm Benzol, Chloroform- o. dgl., enthaltend o, 5 Mol Stickstoffwasserstoffsäure, werden bei einer Temperatur von 35 bis 4o° unter Rühren ioo g Antmonpentachlorid eingetropft. Nach beendeter Umsetzung wird Alkalilauge zugegeben und das Reaktionsprodukt mit Benzol ausgeschüttelt. Der nach Abdestillieren des Benzols hinterbleibende Rückstand wird mit Wasserdampf behandelt, wodurch etwas unveränderter Kampfer sowie entstandenes Kampholensäurenitril entfernt werden. Alsdann wird mit verdünnter Salzsäure angesäuert und das ausfallende Tetrazol mit Äther aufgenommen. Die Ausbeute beträgt 75 110 der Theorie.Differences in the effect of the optically active and the racemic Connections are not detectable as with camphor: The same applies to the only by the melting point of different products, which are made of thujone on the market or can be obtained from pure ß = Thu j an. Example i In a solution of 30.4 g (0.2 mol) of camphor in 250 cc of benzene, chloroform or the like, containing 0.5 mol Hydrazoic acid, at a temperature of 35 to 40 ° with stirring 100 g of anthony pentachloride were added dropwise. After the reaction has ended, it becomes alkali added and the reaction product extracted with benzene. The one after distilling off of the benzene remaining The residue is treated with steam, which removes somewhat unchanged camphor as well as the resulting camphor nitrile will. It is then acidified with dilute hydrochloric acid and the precipitated tetrazole absorbed with ether. The yield is 75 110 of theory.
Die Reinigung des Rohproduktes kann erfolgen durch Umkristallisieren der Quecksilberchloriddoppelverbindung (F.2o8°) aus Wasser oder durch Umkristallisieren des Tetrazols aus Benzol, Äther, Propylalkohol oder verdünnter Salzsäure. Der Festpunkt des reinen Produkts liegt bei 2,42, bis 243°, die Razemverbindung und die optisch aktive Form zeigen keine Unterschiede im Fest-Punkt. Beispiel e In ein Gemisch von 250 ccm 2, 2n-.StiCkstoffivasserstoffsäure und Benzol mit 55 g Zinntetrachlorid und i5 ccm konzentrierter Schwefelsäure werden bei 35 bis 40° 30,49 Japankampfer in Benzol gelöst eingetropft. Das Aufarbeiten geschieht wie bei Beispiel i. Erhalten werden etwa 15 g Karnpfertetrazol vom F. 242 bis 2q.3°. Das Produkt ist linksdrehend. Beispiel 3 In eine Lösung von 30,49 Kampfer in 25o ccm benzolischer Stickstoffwasserstoffsäure werden 8o ccm konzentrierte oder auch z oo°/oige Schwefelsäure unter Rühren eingetropft. Nach dein Aufarbeiten und Entfernung der Nebenprodukte erhält man das Kampfertetrazol in einer Ausbeute von 2o der Theorie. Beispiel 4 16,7 g Thujonoxim, erhalten durch Einwirkung von molaren Mengen Hydroxylamin auf Thujon, gewöhnliches Thujon des Handels (Gemisch von a- und ß-Thuj on), werden in 5o ccm Chloroform und 3 Mol Py ridin gelöst und unter guter Kühlung mit i Mol Benzolsulfonsäurechlorid behandelt. In die Lösung des entstandenen Esters wird i Mol gepulvertes Natriumazid oder i Mol Stickstoffwasserstoffsäure in Chloroform eingetragen. Zuletzt wird die Temperatur auf 5o° gesteigert. Nach Zugeben verdünnter Schwefelsäure wird das Reaktionsprodukt mit Benzol ausgeschüttelt. Das Tetrazol hinterbleibt nach Abdestillieren des Lösungsmittels und wird aus Äther und Petroläther umkristallisiert. Es schmilzt bei 86° und ist leicht löslich in den meisten organischen Lösungsmitteln. Die wäßrige Lösung gibt auf Zusatz von Quecksilberchlorid einen kristallinischen Niederschlag der Ouecksilberchloriddoppelverbindung.The crude product can be purified by recrystallizing the mercury chloride double compound (F.2o8 °) from water or by recrystallizing the tetrazole from benzene, ether, propyl alcohol or dilute hydrochloric acid. The fixed point of the pure product is at 2.42 to 243 °, the racem compound and the optically active form show no differences in the fixed point. EXAMPLE e At 35 ° to 40 °, 30.49 Japanese camphor dissolved in benzene is added dropwise to a mixture of 250 ccm 2, 2N-stick hydrogen and benzene with 55 g tin tetrachloride and 15 cc concentrated sulfuric acid. The work-up takes place as in example i. About 1 5 g of carnpiate tetrazole with a temperature of 242 to 2q.3 ° are obtained. The product rotates to the left. EXAMPLE 3 80 cc of concentrated or 20% sulfuric acid are added dropwise with stirring to a solution of 30.49 of camphor in 250 cc of benzene hydrazoic acid. After working up and removing the by-products, the camphor tetrazole is obtained in a yield of 20% of theory. EXAMPLE 4 1 6.7 g of thujone oxime, obtained by the action of molar amounts of hydroxylamine on thujone, common commercial thujone (mixture of α- and β-thujone), are dissolved in 50 cc of chloroform and 3 mol of pyridine and with good cooling treated with 1 mole of benzenesulfonic acid chloride. One mole of powdered sodium azide or one mole of hydrazoic acid in chloroform is added to the solution of the ester formed. Finally the temperature is increased to 50 °. After adding dilute sulfuric acid, the reaction product is extracted by shaking with benzene. The tetrazole remains after the solvent has been distilled off and is recrystallized from ether and petroleum ether. It melts at 86 ° and is easily soluble in most organic solvents. Upon addition of mercury chloride, the aqueous solution gives a crystalline precipitate of the mercury chloride double compound.
Geht man von reinem ß-Thuj an aus, so erhält man ein Produkt, welches den F. 93 bis 95° zeigt. Beispiel s Eine benzolische Lösung, enthaltend 2,2 Mol Stickstoffwasserstoffsäure, ioo g Zinntetrachlorid und etwa io g konzentrierte Schwefelsäure, wird unter Rühren mit einer Lösung von 32 g Thujon in Benzol versetzt. Die Ausbeute an Thujontetrazol beträgt mehr als 7o 1/o .der Theorie.If you start from pure ß-Thuj, you get a product which shows the F. 93 to 95 °. Example s A benzene solution containing 2.2 mol Hydrazoic acid, 100 g tin tetrachloride and about 10 g concentrated sulfuric acid, a solution of 32 g of thujone in benzene is added while stirring. The yield of thujontetrazole is more than 70 1 / o of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK130899D DE606615C (en) | 1933-07-23 | 1933-07-23 | Process for the preparation of tetrazole pellets of the terpene series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK130899D DE606615C (en) | 1933-07-23 | 1933-07-23 | Process for the preparation of tetrazole pellets of the terpene series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE606615C true DE606615C (en) | 1934-12-06 |
Family
ID=7247249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK130899D Expired DE606615C (en) | 1933-07-23 | 1933-07-23 | Process for the preparation of tetrazole pellets of the terpene series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE606615C (en) |
-
1933
- 1933-07-23 DE DEK130899D patent/DE606615C/en not_active Expired
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