CH311621A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents
Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).Info
- Publication number
- CH311621A CH311621A CH311621DA CH311621A CH 311621 A CH311621 A CH 311621A CH 311621D A CH311621D A CH 311621DA CH 311621 A CH311621 A CH 311621A
- Authority
- CH
- Switzerland
- Prior art keywords
- anilide
- methyl
- diethylamine
- chloro
- fatty acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 7
- 229930195729 fatty acid Natural products 0.000 title claims description 7
- 150000004665 fatty acids Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- YNAFEFREWILTEW-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-2-(diethylamino)propanamide Chemical compound CCN(CC)C(C)C(=O)NC1=C(C)C=CC=C1Cl YNAFEFREWILTEW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003931 anilides Chemical class 0.000 claims description 3
- 239000012230 colorless oil Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000003589 local anesthetic agent Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure (2-halogen-6-methyl-anilids).
Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6 methyl-anilids), welches dadureh gekennzeich- net ist, dass man eine Verbindung der Formel
EMI1.1
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsul- fonyloxy- oder Arylsulfonyloxygruppe, bestehen. Der Austauseh der Gruppe X genen den Diäthylaminrest erfolgt z. B. durch einfaches Erwärmen mit Diäthylamin gegebenenfalls in Gegenwart eines basiseh reagierenden Kondensationsmittels oder von Diäthylamin im tber- schuss. Das a-Diäthylamino-propionsaure- (2- chlor-6-methyl-anilid) ist ein farbloses, unter 0, 04 mm bei 127-130 siedendes Öl. Das IIy-clroehlorid der Base schmilzt bei 215-218" unter Zersetzung.
Das neue Anilid soll als Lokalanästhetikum und als Zwisehenprodukt zur Herstellung wei- terer Derivate Verwendung finden.
Beispiel :
46 Gewichtsteile a-Brom-propionsäure- (2ehlor-6-methyl-anilid) (gewonnen durch Umsetzen von 2-Chlor-6-methyl-anilin mit a-Brom propionyl-ehlorid in Gegenwart von Natriumacetat, Sehmp. 145-147 ) werden in 80 Gewichtsteilen Äthanol suspendiert und mit 36 Gewichtsteilen Diäthylamin versetzt. Die Temperatur steigt dabei leieht an und ein gro#er Teil des Reaktionsgemisehes geht in Lösung.
Nun wird während 4 Stunden bei Zimmer- temperatur gerührt und dann einige Stunden bei Siedetemperatur. Eine Probe mit Wasser und nachfolgend mit verdünnter Salzsäure versetzt ergibt wieder Lösung des ausgefalle- nen Niederschlages. Mit Wasserdampf wird hierauf der Alkohol'und das überschüssige Diäthylamin abgeblasen und nach dem Erkal- ten das zurüekbleibende öl in Ather aufgenommen. Nach dem Trocknen der ätherischen Löstzg und Verjagen des Losungsmittels verbleibt ein öl, das durch Vakuumdestillation gereinigt wird.
Man erhält 39 Gewichtsteile reines a-Diäthylamino-propionsäure- (2-ehlor- 6-methyl-anilid). Die Umsetzung mit Diäthyl- amin kann auch in Benzol stattfinden.
PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6- methyl-anilids), dadurch gekennzeichnet, da# man eine Verbindung der Formel
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
The subject of the present patent is a process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl-anilide), which is characterized by the fact that a compound of the formula
EMI1.1
in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine.
The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X genes the diethylamine residue z. B. by simply heating with diethylamine, optionally in the presence of a basic reacting condensing agent or of diethylamine in excess. The α-diethylamino-propionic acid (2-chloro-6-methyl-anilide) is a colorless oil that boils below 0.04 mm at 127-130. The hydroxyl chloride of the base melts at 215-218 "with decomposition.
The new anilide is to be used as a local anesthetic and as an intermediate product for the production of further derivatives.
Example:
46 parts by weight of a-bromopropionic acid (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with a-bromopropionyl chloride in the presence of sodium acetate, Sehmp. 145-147) suspended in 80 parts by weight of ethanol and treated with 36 parts by weight of diethylamine. The temperature rises and a large part of the reaction mixture goes into solution.
The mixture is then stirred for 4 hours at room temperature and then for a few hours at boiling temperature. A sample with water and then mixed with dilute hydrochloric acid results in a solution of the precipitate. The alcohol and the excess diethylamine are then blown off with steam and, after cooling, the remaining oil is taken up in ether. After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation.
39 parts by weight of pure α-diethylamino propionic acid (2-chloro-6-methyl-anilide) are obtained. The reaction with diethylamine can also take place in benzene.
PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl-anilide), characterized in that a compound of the formula
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311621T | 1952-02-25 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311621A true CH311621A (en) | 1955-11-30 |
Family
ID=25735354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311621D CH311621A (en) | 1952-02-25 | 1952-02-25 | Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311621A (en) |
-
1952
- 1952-02-25 CH CH311621D patent/CH311621A/en unknown
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