CH312572A - Process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl) anilide - Google Patents
Process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl) anilideInfo
- Publication number
- CH312572A CH312572A CH312572DA CH312572A CH 312572 A CH312572 A CH 312572A CH 312572D A CH312572D A CH 312572DA CH 312572 A CH312572 A CH 312572A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- anilide
- 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
- 229930195729 fatty acid Natural products 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 7
- 150000004665 fatty acids Chemical class 0.000 title claims description 7
- 150000003931 anilides Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 14
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003589 local anesthetic agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- FWQUBKZCULDUQS-UHFFFAOYSA-N 2-chloro-n,6-dimethylaniline Chemical compound CNC1=C(C)C=CC=C1Cl FWQUBKZCULDUQS-UHFFFAOYSA-N 0.000 claims description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 2
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 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
- 238000001035 drying Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000001632 sodium acetate Substances 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
- 239000003921 oil Substances 0.000 claims 2
- 239000012230 colorless oil Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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-6methyl-anilids), welches dadurch gekennzeichnet 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 basisehen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfonyloxy-oder Arylsulfonyloxygruppe bestehen. Der Austausch der Gruppe X gegen den Diäthylaminrest erfolgt zum Beispiel durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basiseh reagierenden Kondensationsmittels oder von Diäthylamin im Überschuss.
Das Diäthylaminoacet-N-methyl- (2-chlor- 6-methyl-anilid) ist ein farbloses, unter 0, 35 mm Hg bei 127-130 siedendes 61. Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.
Beispiel
23 Gewichtsteile Chloracet-N-methyl- (2 chlor-6-methyl-anilid) (gewonnen durch Umsetzen von N-Methyl-2-chlor-6-methyl-anilin mit Chloracetyleblorid in Gegenwart von Na triumacetat) werden in 40 Gewichtsteilen Äthanol suspendiert und mit 20 Gewichtstei- len Diäthylamin versetzt.
Die Temperatur steigt dabei leicht an, und ein grosser Teil des Reaktionsgemisches geht in Losung. Nun wird während 4 Stunden bei Zimmertemperatur gerührt, dann 3 Stunden bei 45-50 und endlich 4 Stunden bei 65-75". Mit Wasserdampf wird hierauf der Alkohol und das übersehüssige Diäthylamin abgeblasen und naeh dem Erkalten das zuriiekbleibende öl in Äther aufgenommen. Nach dem Trocknen der ätheri- schen Losung und Verjagen des Losungsmit- tels verbleibt ein öl, das durch Vakuumdestil- lation gereinigt wird. Man erhält 22 Gewichts- teile reines Diäthylaminoessigsäure-N-methyl (2-chlor-6-methyl-anilid).
Die Umsetzung mit Diäthylamin kann auch in Benzol stattfinden.
PATENTANSPRUCH
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure- (2-halogen-6-
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl) anilide
The subject of the present patent is a process for the preparation of a new basic substituted fatty acid (2-halo-6methyl-anilide), which is characterized in 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 e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group. Group X is exchanged for the diethylamine residue, for example, by simply heating with diethylamine, optionally in the presence of a condensing agent which reacts on a basic basis or of excess diethylamine.
The diethylaminoacet-N-methyl- (2-chloro-6-methyl-anilide) is a colorless 61 boiling below 0.35 mm Hg at 127-130. The new anilide is said to be used as a local anesthetic and as an intermediate for the production of other derivatives .
example
23 parts by weight of chloroacet-N-methyl- (2 chloro-6-methyl-anilide) (obtained by reacting N-methyl-2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate) are suspended in 40 parts by weight of ethanol and treated with 20 parts by weight of diethylamine.
The temperature rises slightly, and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature, then 3 hours at 45-50 and finally 4 hours at 65-75 ". The alcohol and the excess diethylamine are then blown off with steam and, after cooling, the remaining oil is absorbed in ether Drying the ethereal solution and driving off the solvent leaves an oil that is purified by vacuum distillation, giving 22 parts by weight of pure N-methyl (2-chloro-6-methyl-anilide) diethylaminoacetic acid.
The reaction with diethylamine can also take place in benzene.
PATENT CLAIM
Process for the production of a new basic substituted fatty acid (2-halogen-6-
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312572T | 1952-11-25 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH312572A true CH312572A (en) | 1956-01-15 |
Family
ID=25735444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH312572D CH312572A (en) | 1952-11-25 | 1952-11-25 | Process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl) anilide |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH312572A (en) |
-
1952
- 1952-11-25 CH CH312572D patent/CH312572A/en unknown
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