CH131285A - Process for the preparation of a polysulfide ester of an aromatic carboxylic acid. - Google Patents
Process for the preparation of a polysulfide ester of an aromatic carboxylic acid.Info
- Publication number
- CH131285A CH131285A CH131285DA CH131285A CH 131285 A CH131285 A CH 131285A CH 131285D A CH131285D A CH 131285DA CH 131285 A CH131285 A CH 131285A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- carboxylic acid
- aromatic carboxylic
- ester
- acid
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 229920001021 polysulfide Polymers 0.000 title claims description 4
- 239000005077 polysulfide Substances 0.000 title claims description 4
- 150000008117 polysulfides Polymers 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- -1 sulfur halide Chemical class 0.000 claims description 4
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 239000012021 ethylating agents Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- CAIKKJIIZHDMSX-UHFFFAOYSA-N ethyl 2-sulfanylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1S CAIKKJIIZHDMSX-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Polysulfidesters einer aromatischen Carbonsäure. Gegenstand vorliegender Erfindung ist ein Verfahren zur Darstellung eines Poly- sulfidesters einer aromatischen Carbonsäure, dadurch gekennzeichnet, dass man 2-Mer- kaptobenzoesäure, ein Xthylierungsmittel und ein Schwefelhalogenid aufeinander ein wirken lässt.
Man kann zum Beispiel die 2-Merkapto- benzoesäure zunächst nach den üblichen 3Ie- thoden in ihren Äthylester überführen und diesen mit einem Schwefelhalogenid, zum Beispiel Schwefelchlorid, SCh, umsetzen, oder aber zunächst durch Umsetzung der 2- lZerkaptobenzoesäure mit einem Schwefel halogenid, zum Beispiel Schwefelchlorid, das Di-Benzoesäure-2,
2'-trisulfid gewinnen und dieses in üblicher Weise verestern-. In beiden Fällen gelangt man zum Di-Benzoesäure- äthylester-2,2'-trisulfid der Formel
EMI0001.0026
Das so erhaltene Di-Benzoesäureäthvl- ester-2,2'-trisulficl lässt sich aus Alkohol-Ben- zin umkristallisieren und bildet feine, weisse Nadeln vom F. P. 108 bis<B>110</B> .
Das neue Produkt soll zu therapeutischen Zwecken verwendet werden.
Beispiel <I>Z:</I> 30 Gewichtsteile 2-1blerliaptobenzoesäure werden in280GewichtsteilenabsolutemÄthyl- alkohol, der 4 % HCl-gas enthält, gelöst und einige Stunden am Rückfluss gekocht. Hier auf wird der Alkohol zum grösseren Teil ab destilliert, den Rest giesst man in Wasser, nimmt den ausgeschiedenen Ester in Äther auf, schüttelt mit Bicarbonat, trocknet mit Natriumsulfat und verdampft den Äther. Der Ester wird im Vakuum destilliert; er siedet bei einem Druck von 12 mm bei 138 bis 139 .
Er stellt eine kräftig esterartig riechende, farblose, ölige Flüssigkeit dar.
10,7 Gewichtsteile des so erhaltenen Mer- kaptobenzoesäureäthylesters werden in Me- thylenchlorid gelöst und allmählich unter Kühlung mit 3,5 Gewichtsteilen Schwefel chlorid in 11Iethy lenchloridlösung versetzt. Das Trisulfid scheidet sich nach kurzem Er wärmen des Reaktionsbemisches auf dem Wasserbad und Abdunsten des Lösungsmit tels fest ab. Durch Umkristallisieren aus Al kohol-Benzin wird es gereinigt.
<I>Beispiel 2:</I> 5 (-xewichtsteile 2-llerl@aptol)enzoesäure werden in 141-ethylenchlorid gelöst und in die gekühlte Lösung unter Rühren allmählich etwa 1,7 Gewichtsteile Schwefelchlorid, in 1Zethylenchlorid gelöst, zutropfen gelassen. Die HCl-Abspaltung wird durch schwaches Erwärmen auf dem Wasserbad beendigt. Dann wird filtriert, der Rückstand mit Ace ton ausgeschüttelt und mit. Alkohol ausge kocht.
Nach dem Trocknen bildet das Di- Benzoesäure-2,2'-trisulfid ein schwach gelb gefärbtes Pulver vom F. P. 302 bis 304 ; in organischen Lösungsmitteln ist es schwer löslich. .
Das so erhaltene Di- Benzoesäure-2,2'-tri- sulficl wird in absolutem Alkohol gelöst, HCl- gas eingeleitet, die Lösunb auf demWasser- ba.d 3 Stunden erwärmt, der Alkohol teil weise abdestilliert und die konzentrierte Lö sung im Vakuum über Natrankalk von den Resten von Alkohol und Säure befreit.
Es wird ein Trisulfid erhalten, das in seiner Zu- sammen2#etzung und seinen Eigenschaften. mit dem nach Beispiel 1 erhaltenen Produkt iden- tiscli ist.
Process for the preparation of a polysulfide ester of an aromatic carboxylic acid. The present invention relates to a process for the preparation of a polysulfide ester of an aromatic carboxylic acid, characterized in that 2-mercaptobenzoic acid, an ethylating agent and a sulfur halide are allowed to act on one another.
For example, 2-mercaptobenzoic acid can first be converted into its ethyl ester according to the usual 3Ie- thoden and this react with a sulfur halide, for example sulfur chloride, SCh, or by reacting 2-lzerkaptobenzoic acid with a sulfur halide Example sulfur chloride, the di-benzoic acid-2,
Gain 2'-trisulfide and esterify this in the usual way. In both cases, the di-benzoic acid ethyl ester-2,2'-trisulfide of the formula is obtained
EMI0001.0026
The di-benzoic acid ether-2,2'-trisulficl obtained in this way can be recrystallized from alcohol-gasoline and forms fine, white needles from F.P. 108 to <B> 110 </B>.
The new product is intended to be used for therapeutic purposes.
Example <I> Z: </I> 30 parts by weight of 2-liter liaptobenzoic acid are dissolved in 280 parts by weight of absolute ethyl alcohol containing 4% HCl gas and refluxed for a few hours. Here, the majority of the alcohol is distilled off, the rest is poured into water, the precipitated ester is absorbed in ether, shaken with bicarbonate, dried with sodium sulfate and the ether is evaporated. The ester is distilled in vacuo; it boils at 138 to 139 at a pressure of 12 mm.
It is a colorless, oily liquid that smells strongly like ester.
10.7 parts by weight of the ethyl mercaptobenzoate obtained in this way are dissolved in methylene chloride, and 3.5 parts by weight of sulfur chloride in methylene chloride solution are gradually added while cooling. The trisulfide separates out after a short time He warms the reaction mixture on the water bath and evaporates the solvent from solid. It is purified by recrystallizing it from alcohol gasoline.
Example 2: 5 parts by weight of 2-llerl @ aptol) enzoic acid are dissolved in 141-ethylene chloride and about 1.7 parts by weight of sulfur chloride, dissolved in 1-methylene chloride, are gradually added dropwise to the cooled solution while stirring. The elimination of HCl is ended by gentle warming on a water bath. It is then filtered, the residue is extracted with acetone and extracted with. Boiled alcohol.
After drying, the di-benzoic acid-2,2'-trisulphide forms a pale yellow colored powder of F. P. 302 to 304; it is sparingly soluble in organic solvents. .
The di-benzoic acid-2,2'-trisulficl obtained in this way is dissolved in absolute alcohol, HCl gas is passed in, the solution is heated on the water bath for 3 hours, the alcohol is partially distilled off and the concentrated solution is in vacuo The residues of alcohol and acid are removed using soda lime.
A trisulphide is obtained which, in its composition and its properties. with the product obtained according to Example 1 is identical.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH129730T | 1927-05-27 | ||
| CH131285T | 1927-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH131285A true CH131285A (en) | 1929-01-31 |
Family
ID=25711315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH131285D CH131285A (en) | 1927-05-27 | 1927-05-27 | Process for the preparation of a polysulfide ester of an aromatic carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH131285A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0480270A1 (en) * | 1990-10-06 | 1992-04-15 | CASSELLA Aktiengesellschaft | Arylsulfides and process for their fabrication |
-
1927
- 1927-05-27 CH CH131285D patent/CH131285A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0480270A1 (en) * | 1990-10-06 | 1992-04-15 | CASSELLA Aktiengesellschaft | Arylsulfides and process for their fabrication |
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