CH267955A - Process for the preparation of a new amine. - Google Patents
Process for the preparation of a new amine.Info
- Publication number
- CH267955A CH267955A CH267955DA CH267955A CH 267955 A CH267955 A CH 267955A CH 267955D A CH267955D A CH 267955DA CH 267955 A CH267955 A CH 267955A
- Authority
- CH
- Switzerland
- Prior art keywords
- dependent
- amine
- compound
- preparation
- chloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000001412 amines Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Amins. Es wurde gefunden, dass man ein neues Amin erhält, wenn man eine Verbindung der Formel
EMI0001.0001
mit einer Verbindung der Formel (C2H5) . . N. CH.- <B><U>CH..</U></B> Y , wobei X und Y bei dem Reaktion sich abspal tende Reste bedeuten, umsetzt, so z. B. N-(p- Chlor-ben7yl)-p-chlor-anilin bzw. eine seiner N-Metall-, wie N-Alkalimetallverbindungen, mit ss-Oxy-äthyldiäthylamin bzw. einem seiner reaktionsfähigen Ester, wie z. B. einem ss-Halogen-äthyldiäthylamin.
Die genannte Umsetzung kann in An- oder Abwesenheit von Verdünnungsmitteln und/oder Kondensationsmitteln oder Kataly satoren durchgeführt werden. Als Verdün nungsmittel lasen sich z. B. Alkohole, Essig ester, Dioxan, Benzol, Tohtol, Nitrobenzol und dergleichen verwenden. Als Kondensations mittel seien Alkalien und deren Derivate wie Alkaliamide, Phenylalkalien, ferner Phos- phoroxyhalogenide, Phosphorpentoxyd oder Zinkchlorid genannt. Als Katalysator eignet sieh z. B. Kupferpulver.
Verbindungen der genannten Formeln sind zum Teil bekannt. Sie lassen sich nach an sich bekannten Metho den gewinnen.
Das erfindungsgemäss erhaltene N-(ss-Di- äthylamino-äthyl)-N-(p-chlor-benzyl) -p-chlor- anilin siedet unter 0,07 mm Druck bei 170 bis 181 . Das Amin bildet wasserlösliche Salze z. B. mit. Phosphorsäure, Salzsäure und Schwe felsäure.
Durch Umsetzung z. B. mit Methylbromid n Essigester bildet sich das Brommethylat vom Smp. 157 .
Das Amin soll als Heilmittel oder als Zwi schenprodukt Verwendung finden.
<I>Beispiel 1:</I> 125 Gew.-Teile N-(p-Chlor-ben7,yl)-p-chlor- anilin werden zusammen mit 70 Gew.-Teilen /3 Chlor-äthyldiäthylamin langsam unter Rüh ren erwärmt, wobei bei etwa 80 Lösung ein tritt; bei weiterem Erwärmen wird die Reak- tionsmasse wieder fest. Zum Schluss erhitzt man noch auf 150 , gibt nach dem Abkühlen Wasser, Alkalilauge und Äther zu, wäscht die ätherische Lösung, trocknet, dampft ein und destilliert den Rückstand.
Es wird so das N- (ss-Diäthylamino-äthyl)-N-(p-chlor-benzyl) -p- ehlor-anilin vom Kp. 0,07 170 bis 181 erhal ten. Das Amin bildet wasserlösliche Salze z. B. mit Phosphorsäure, Salzsäure und Schwefelsäure.
<I>Beispiel 2:</I> 51 Gew.-Teile N-(p-Chlor-ben7yl)-p-chlor- anilin, 200 Vol.-Teile Toluol und 10 Gew.- Teile Natriumamid werden 4 Stunden am Rückfluss unter Stickstoff erwärmt, wobei Ammoniakgas entweicht.
Nachdem das Na triumsalz der oben erwähnten Base gebildet ist, gibt man 42 Gew.-Teile ss-Chlor-äthyldi- äthy lamin langsam hinzu und erwärmt noch bis zur beendeten Umsetzung. Hierauf wird die abgekühlte Toluollösung mit Wasser ge waschen, getrocknet, eingedampft und der Rückstand destilliert. Man erhält so die in Beispiel 1 beschriebene Base.
Process for the preparation of a new amine. It has been found that a new amine is obtained if a compound of the formula
EMI0001.0001
with a compound of the formula (C2H5). . N. CH.- <B><U>CH..</U> </B> Y, where X and Y mean residues splitting off in the reaction, converts, for example. B. N- (p-chloro-ben7yl) -p-chloro-aniline or one of its N-metal, such as N-alkali metal compounds, with ss-oxy-ethyl diethylamine or one of its reactive esters, such as. B. a ss-halo-ethyl diethylamine.
The reaction mentioned can be carried out in the presence or absence of diluents and / or condensing agents or catalysts. As a diluent read z. B. use alcohols, ethyl acetate, dioxane, benzene, Tohtol, nitrobenzene and the like. Alkalis and their derivatives such as alkali amides, phenylalkali, and also phosphorus oxyhalides, phosphorus pentoxide or zinc chloride may be mentioned as condensation agents. As a catalyst see z. B. copper powder.
Some of the compounds of the formulas mentioned are known. They can be obtained using methods known per se.
The N- (ss-diethylamino-ethyl) -N- (p-chlorobenzyl) -p-chloroaniline obtained according to the invention boils at 170 to 181 under 0.07 mm pressure. The amine forms water-soluble salts e.g. B. with. Phosphoric acid, hydrochloric acid and sulfuric acid.
By implementing z. B. with methyl bromide n ethyl acetate forms the bromomethylate with a melting point of 157.
The amine is said to be used as a remedy or as an intermediate product.
<I> Example 1: </I> 125 parts by weight of N- (p-chloro-ben7, yl) -p-chloro-aniline are slowly heated with stirring together with 70 parts by weight / 3 chloroethyl diethylamine , with solution occurring at about 80; with further heating the reaction mass solidifies again. Finally, the mixture is heated to 150, after cooling, water, alkali lye and ether are added, the ethereal solution is washed, dried, evaporated and the residue is distilled.
It is thus the N- (ss-diethylamino-ethyl) -N- (p-chloro-benzyl) -p- ehloraniline of boiling point 0.07 170 to 181 th. The amine forms water-soluble salts z. B. with phosphoric acid, hydrochloric acid and sulfuric acid.
<I> Example 2: </I> 51 parts by weight of N- (p-chloro-ben7yl) -p-chloroaniline, 200 parts by volume of toluene and 10 parts by weight of sodium amide are refluxed for 4 hours Nitrogen is heated, with ammonia gas escaping.
After the sodium salt of the abovementioned base has been formed, 42 parts by weight of ß-chloro-ethyldiethy lamin are slowly added and the mixture is heated until the reaction has ended. The cooled toluene solution is then washed with water, dried and evaporated, and the residue is distilled. The base described in Example 1 is thus obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267955T | 1946-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267955A true CH267955A (en) | 1950-04-30 |
Family
ID=4476686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267955D CH267955A (en) | 1946-12-21 | 1946-12-21 | Process for the preparation of a new amine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267955A (en) |
-
1946
- 1946-12-21 CH CH267955D patent/CH267955A/en unknown
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