DE1078581B - Process for the production of 1, 3-Dioxolanyl- (4) -methylaethern of o-Vanillinsaeuramiden - Google Patents
Process for the production of 1, 3-Dioxolanyl- (4) -methylaethern of o-VanillinsaeuramidenInfo
- Publication number
- DE1078581B DE1078581B DER22901A DER0022901A DE1078581B DE 1078581 B DE1078581 B DE 1078581B DE R22901 A DER22901 A DE R22901A DE R0022901 A DER0022901 A DE R0022901A DE 1078581 B DE1078581 B DE 1078581B
- Authority
- DE
- Germany
- Prior art keywords
- dioxolanyl
- vanillic acid
- aliphatic
- acid amides
- alkyl
- 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 3
- AUZQQIPZESHNMG-UHFFFAOYSA-N 3-methoxysalicylic acid Chemical compound COC1=CC=CC(C(O)=O)=C1O AUZQQIPZESHNMG-UHFFFAOYSA-N 0.000 claims description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims description 3
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- -1 cycloalkyl radicals Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000005217 methyl ethers Chemical class 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 1,3-Dioxolanyl-(4)-methyläthern von o-Vanillinsäureamiden Die Methyläther von o-Vanillinsäuredimethylamid und o-Vanillinsäurediäthylamid sind bekannt. Diese Methyläther üben eine anregende Wirkung auf Kreislauf und Atmung aus. Process for the preparation of 1,3-dioxolanyl- (4) -methyl ethers of o-Vanillinsäureamiden The methyl ethers of o-Vanillinsäuredimethylamid and o-Vanillinsäurediäthylamid are known. These methyl ethers have a stimulating effect on circulation and breathing the end.
Es wurde demgegenüber gefunden, daß 1,3-Dioxolanyl-(4)-methyläther von o-Vanillinsäureamiden der allgemeinen Formel in der R1 ein Wasserstoff- oder Halogenatom oder eine Nitrogruppe, R2 und R3 Wasserstoffatome, Alkyl-, Oxyalkyl- oder Cycloalkylreste sowie R4 und R5 Wasserstoffatome, Alkyl- oder Arylreste bedeuten, überraschenderweise eine ausgeprägte narkotische und sedative Wirkung besitzen.In contrast, it has been found that 1,3-dioxolanyl- (4) -methyl ethers of o-vanillic acid amides of the general formula in which R1 is a hydrogen or halogen atom or a nitro group, R2 and R3 are hydrogen atoms, alkyl, oxyalkyl or cycloalkyl radicals and R4 and R5 are hydrogen atoms, alkyl or aryl radicals, surprisingly have a pronounced narcotic and sedative effect.
Erfindungsgemäß werden die genannten 1,3-Dioxolanyl-(4)-methyläther von o-Vanillinsäureamiden erhalten, wenn man o-Vanillinsäureamide der allgemeinen Formel in der R1, R2 undR3 die angegebene Bedeutung haben, mit Glycerinmonochlorhydrin in an sich bekannter Weise, z. B. in Gegenwart von Natriumäthylat, umsetzt und die erhaltenen Glycerinäther in an sich bekannter Weise mit aliphatischen, aromatischen oder aliphatisch-aromatischen Aldehyden oder Ketonen zur Reaktion bringt.According to the invention, said 1,3-dioxolanyl- (4) -methyl ethers are obtained from o-vanillic acid amides if o-vanillic acid amides of the general formula in which R1, R2 andR3 have the meaning given, with glycerol monochlorohydrin in a manner known per se, e.g. B. in the presence of sodium ethylate, and the glycerol ether obtained reacts in a manner known per se with aliphatic, aromatic or aliphatic-aromatic aldehydes or ketones.
Die Ringschlußreaktion zu den 1,3-Dioxolanverbindungen wird in an sich bekannter Weise durch Zusatz saurer Katalysatoren, wie Salz.säure oder Toluolsulfonsäure, gefördert. Man kann auch in Gegenwart eines höher siedenden Lösungsmittels arbeiten und das bei der Verätherung entstehende Wasser durch azeotrope Destillation entfernen. The ring closure reaction to the 1,3-dioxolane compounds is in on known way by adding acidic catalysts, such as hydrochloric acid or toluenesulfonic acid, promoted. You can also work in the presence of a higher-boiling solvent and remove the water resulting from the etherification by azeotropic distillation.
Beispiel o-Vanillinsäureamid, Glycerinmonochlorhydrin und Natriumäthylat werden in molaren Mengen in Äthanol umgesetzt. Vom ausgefallenen Natriumchlorid wird abfiltriert und das Filtrat auf ein Viertel seines Volumens eingedampft. Den nach dem Erkalten abgesaugten Glycerinäther kristallisiert man aus Chloroform um. Example o-vanillic acid amide, glycerol monochlorohydrin and sodium ethylate are reacted in molar amounts in ethanol. From the precipitated sodium chloride is filtered off and the filtrate is evaporated to a quarter of its volume. The After cooling off, the glycerol ether sucked off is recrystallized from chloroform.
Ausbeute 45 °/o der Theorie. F. 99 bis 1000 C; sehr leicht löslich in Wasser.Yield 45% of theory. M.p. 99 to 1000 C; very easily soluble in water.
16,5 g des o-Vanillinsäureamid-1-glycerinäthers werden in 135 ccm Aceton, das 1 °/o Chlorwasserstoff enthält, gelöst und in Gegenwart von 10log wasserfreiem Natriumsulfat 14 Stunden bei Zimmertemperatur gerührt. Das Reaktionsgut wird dann durch Einleiten von Ammoniak auf Pn 7 eingestellt. Ausfallende anorganische Salze werden abgesaugt, dann wird die Lösung mit Kohle behandelt und das Lösungsmittel verdampft. Der Rückstand wird aus wäßrigem Methanol umkristallisiert. Der Äther aus 2-Dimethyl-4-oxymethyl-1,3-dioxolan und o-Vanillinsäureamid fällt in einer Ausbeute von 1 1?9 g, entsprechend 60°/o der Theorie, in farblosen Kristallen an und schmilzt bei 85 bis 860 C. 16.5 g of the o-vanillic acid amide-1-glycerol ether are in 135 ccm Acetone, which contains 1% of hydrogen chloride, dissolved and in the presence of 10log of anhydrous Sodium sulfate stirred for 14 hours at room temperature. The reaction mixture is then adjusted to Pn 7 by introducing ammonia. Failing inorganic salts are suctioned off, then the solution is treated with charcoal and the solvent evaporates. The residue is recrystallized from aqueous methanol. The ether from 2-dimethyl-4-oxymethyl-1,3-dioxolane and o-vanillic acid amide precipitates in one yield of 1 1? 9 g, corresponding to 60% of theory, in colorless crystals and melts at 85 to 860 C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER22901A DE1078581B (en) | 1958-03-15 | 1958-03-15 | Process for the production of 1, 3-Dioxolanyl- (4) -methylaethern of o-Vanillinsaeuramiden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER22901A DE1078581B (en) | 1958-03-15 | 1958-03-15 | Process for the production of 1, 3-Dioxolanyl- (4) -methylaethern of o-Vanillinsaeuramiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1078581B true DE1078581B (en) | 1960-03-31 |
Family
ID=7401250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER22901A Pending DE1078581B (en) | 1958-03-15 | 1958-03-15 | Process for the production of 1, 3-Dioxolanyl- (4) -methylaethern of o-Vanillinsaeuramiden |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1078581B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2566773A1 (en) * | 1984-06-28 | 1986-01-03 | Bristol Myers Co | NOVEL SUBSTITUTED BENZAMIDES, PROCESSES FOR PREPARING THESE COMPOUNDS, AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
| US5011992A (en) * | 1984-06-28 | 1991-04-30 | Bristol-Myers Squibb Company | Pharmacologically active substituted benzamides |
-
1958
- 1958-03-15 DE DER22901A patent/DE1078581B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2566773A1 (en) * | 1984-06-28 | 1986-01-03 | Bristol Myers Co | NOVEL SUBSTITUTED BENZAMIDES, PROCESSES FOR PREPARING THESE COMPOUNDS, AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
| US5011992A (en) * | 1984-06-28 | 1991-04-30 | Bristol-Myers Squibb Company | Pharmacologically active substituted benzamides |
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