CH311611A - 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
- CH311611A CH311611A CH311611DA CH311611A CH 311611 A CH311611 A CH 311611A CH 311611D A CH311611D A CH 311611DA CH 311611 A CH311611 A CH 311611A
- Authority
- CH
- Switzerland
- Prior art keywords
- anilide
- methyl
- fatty acid
- halogen
- substituted fatty
- Prior art date
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- 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 bil det ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6- methyl-anilids), welches dadurch gekennzeich net ist, d'ass man eine Verbindung der Formel
EMI0001.0010
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit. n-Butylamin umsetzt..
Der Rest X kann. in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähi gen Substituenten, wie z. B. einer A.lkylsul- tonploxy- oder Arylsulfonyloxygruppe, beste hen. Der Austausch der Gruppe X gegen den n-Butylaminrest erfolgt, z.
B. durch einfaches Erwärmen mit n-Butylamin gegebenenfalls in Gegenwart eines basisch reagierenden Konden sationsmittels oder von n-Butylamin im L ber- schuss. Das n-Butylamino-aeet-(2-chlor-6-me- thy1-a.nilid) ist. ein farbloses, unter 0,02 mm Hg bei 140-143 siedendes öl. Das Hydroehlorid der Base schmilzt bei 231-233 .
Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. <I>Beispiel:</I> 50 Gewichtsteile Chloracet-(2-chlor-6-me- thyl-anilid) (gewonnen dureh Umsetzen von 2- (,'hlor-6-methyl-anilin mit Chloracetylchlorid in Gegenwart von Na.triumacetat, Schmp. 140 bis 141 )
werden in 100 Gewiehtsteilen Ben zol suspendiert und mit 150 Gewichtsteilen n-Butylamin versetzt. Die Temperatur steigt dabei leicht an und ein grosser Teil des Reak tionsgemisches geht. in Lösung. Nun wird während 4 Stunden bei Zimmertemperatur ge rührt und dann einige Stunden bei 60-65 . Das überschüssige Butylamin wird abdestil- liert, der Rückstand mit Natronlauge versetzt und das sich abscheidende<B>öl</B> in Äther aufge nommen.
Nach dem Trocknen der ätherischen Lösung und Verjagen des Lösungsmittels ver bleibt ein öl, das durch Vakuumdestillation gereinigt. wird. Ma.n erhält. 55 Gewichtsteile reines n-But.,ylaminoacet-(2-chlor-6-metltyl- anilid), was einer Ausbeute von 93 /o- ent spricht.
Process for the production of a new basic substituted fatty acid. (2-halogen.6-methyl-anilide). The subject of the present patent bil det a process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl-anilide), which is characterized by having a compound of the formula
EMI0001.0010
in which X denotes a reactive radical which is split off during the reaction, with. n-butylamine converts.
The rest of X can. in a halogen atom or other reactive substituents suitable for replacement with the basic radical, such as. B. an A.lkylsul- tonploxy or arylsulfonyloxy group, best hen. The group X is exchanged for the n-butylamine residue, e.g.
B. by simply heating with n-butylamine, optionally in the presence of a basic condensation agent or n-butylamine in excess. The n-butylamino-aeet- (2-chloro-6-methy1-a.nilid) is. a colorless oil boiling below 0.02 mm Hg at 140-143. The hydrochloride of the base melts at 231-233.
The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 50 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2- (, 'chloro-6-methyl-aniline with chloroacetyl chloride in the presence of Na. trium acetate, melting point 140 to 141)
are suspended in 100 parts by weight of benzene and mixed with 150 parts by weight of n-butylamine. The temperature rises slightly and a large part of the reaction mixture goes. in solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at 60-65. The excess butylamine is distilled off, sodium hydroxide solution is added to the residue and the <B> oil </B> which separates out is taken up in ether.
After the essential solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation. becomes. You get. 55 parts by weight of pure n-but., Ylaminoacet- (2-chloro-6-methyl-anilide), which corresponds to a yield of 93%.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH311611T | 1952-02-25 | ||
CH307799T | 1952-11-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311611A true CH311611A (en) | 1955-11-30 |
Family
ID=25735344
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311611D CH311611A (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 |
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CH (1) | CH311611A (en) |
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US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10842798B1 (en) | 2019-11-06 | 2020-11-24 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10927096B2 (en) | 2019-03-11 | 2021-02-23 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10934263B2 (en) | 2019-03-11 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10968179B2 (en) | 2019-03-11 | 2021-04-06 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US11332446B2 (en) | 2020-03-11 | 2022-05-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
-
1952
- 1952-02-25 CH CH311611D patent/CH311611A/en unknown
Cited By (14)
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US11377422B2 (en) | 2019-03-11 | 2022-07-05 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10934263B2 (en) | 2019-03-11 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US11643404B2 (en) | 2019-03-11 | 2023-05-09 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
US10927096B2 (en) | 2019-03-11 | 2021-02-23 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
US11603355B2 (en) | 2019-03-11 | 2023-03-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10968179B2 (en) | 2019-03-11 | 2021-04-06 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US11512058B2 (en) | 2019-03-11 | 2022-11-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10842798B1 (en) | 2019-11-06 | 2020-11-24 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US11696912B2 (en) | 2019-11-06 | 2023-07-11 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US11332446B2 (en) | 2020-03-11 | 2022-05-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
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