CH98666A - Process for the preparation of a therapeutically valuable ester from trichloroethyl alcohol. - Google Patents
Process for the preparation of a therapeutically valuable ester from trichloroethyl alcohol.Info
- Publication number
- CH98666A CH98666A CH98666DA CH98666A CH 98666 A CH98666 A CH 98666A CH 98666D A CH98666D A CH 98666DA CH 98666 A CH98666 A CH 98666A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- alcohol
- preparation
- trichloroethyl
- therapeutically valuable
- Prior art date
Links
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FDEQQCOTLPPCAO-UHFFFAOYSA-N Cl.OC(O)=O Chemical compound Cl.OC(O)=O FDEQQCOTLPPCAO-UHFFFAOYSA-N 0.000 description 1
- 241000188250 Idas Species 0.000 description 1
- 101150057104 MCIDAS gene Proteins 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- -1 trichloroisopropyl alcohol Chemical compound 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines therapeutisch wert-vollen Esters aus Trichloräthylalkohol. Es wurde gefunden, dass man durch Um- wa,ndlung des TriGhlorätliylalkohols in !den Karb-aminsäcareester zu einem wertvollen neuen Schlafmittel gelangt, bei demdie wirk- sa,men und toxisellen Dosen weitauseinander liegen.
Diese Tatsa#c'he ist umso überraschen der, als bekanntlich der Toxiziiätsquotient bei,dem Triehlor'Mhyla.lkohol ein viel s,elileeh- terer ist, wie zum Beispiel bei dem ho-moiogen Trichlorisopropylalkohol (Ther. Monatshefte <B>1903,</B> Seite 474), währendtlas Verhältnis bei den Urethanen. sich als gerade umgekehrt herausgestellt hat.
Zur Herstellung der neuen Verbindung verfäUrt man so, dass man Trichloräthylalko- hol, Phosgen und Ammoniakaufeinander zur Einwirkung bringt. Man kann so verfahren, .dass man zuerst Phosgen und Ammoniak zu ]Ela,rnsto#ffe,lilorid vereinigt und dieses !dann auf Triehlorätliylalkoliol zur Einwirkung bringt.
Man kann auch zuerst Phosgen auf Trichloräthylalkohol einwirken lassen und das Produkt dann mit Ammonia,1-, umsetzen. <I>Beispiel<B>1:</B></I> Zu einer Auflösung von Trielilorätllyl- alkohol in wasserfreiein Äther fügt man die äquimolekulare Menge Harnstoffühlorid, das ebenfalls in wasserfreiem Äther gelöst ist.
Nach Stehen über Nacht wird,der Äther aus der eventuell filtrierten Lösung abdestilliert und der Rückstand durch Umlösen aus Pe- trolätlier gereinigt.
Die tberführung vollzieht sich nach. der Reaktionsgleichung: <B>1.</B> CCI,-CII,011+CI-CONH,= CCI,-CH,0-CONH,+HCI. Man erhält auf diese Weise Idas Urethan ,des Trichloräthylalkoho-ls in s6hönen weissen Nadeln vom Schmelzpunkt 64 bis<B>65'.</B> Es ist leicht löslich in Alkohol und Äther. In Wasser von Zimmertemperautur löst es sich <B>zu</B> etwa<B>1</B> ?7o.
<I>Beispiel 2:</I> Zu einem Gemisch von molekularen Men gen Trielilorätliylalkohol und Chinolin in benzolischer Lösung fügt man ein Molekül
EMI0002.0001
Phosgen <SEP> in <SEP> Benzol <SEP> gelöst <SEP> nach <SEP> und <SEP> nach <SEP> zu.
<tb> Na,ch <SEP> mehrtägigem <SEP> Stehen <SEP> wird <SEP> Eiswasser
<tb> zugesetzt <SEP> und <SEP> das <SEP> Chinolin <SEP> mit <SEP> stark <SEP> ver dünnter <SEP> Salzsäure <SEP> ausgeschüttelt.
<SEP> Die <SEP> über
<tb> Chlorcalaium <SEP> getrocknete <SEP> Lösung, <SEP> die <SEP> das
<tb> Chlorharbonat <SEP> des <SEP> Trichloräthylalkohols <SEP> ent hält, <SEP> liefert <SEP> bei <SEP> der <SEP> Umsetzung <SEP> mit <SEP> Ammo niak <SEP> ebenfalls <SEP> das <SEP> in <SEP> Beispiel <SEP> <B>1</B> <SEP> beschriebene
<tb> Urethan, <SEP> das <SEP> in <SEP> der <SEP> üblichen <SEP> Weise <SEP> isoliert
<tb> und <SEP> gereinigt <SEP> wird.
<tb>
Die <SEP> Überführung <SEP> vollzieht <SEP> sich <SEP> nach <SEP> den
<tb> Reaktionsgleieliungen 2a) <SEP> cc12-CH2OH+Coc12=
<tb> cci#,-CH,-0-COCI+IICI;
<tb> <B>2b) <SEP> CCI=CHIO-COCI+NH3=</B>
<tb> <B>CCI.-CH2O-CONH2+HCI.</B>
Process for the preparation of a therapeutically valuable ester from trichloroethyl alcohol. It has been found that by converting the tri-chloroethyl alcohol into the carbamine acid ester, a valuable new sleeping aid is obtained in which the effective and toxic doses are far apart.
This fact is all the more surprising because, as is well known, the toxicity quotient in the case of the triehlor'mhyla alcohol is much more elusive, as for example in the case of the homogeneous trichloroisopropyl alcohol (Ther .monthshefte <B> 1903, </B> Page 474), while the ratio for urethanes. turned out to be just the opposite.
To prepare the new compound, the procedure is to bring trichloroethyl alcohol, phosgene and ammonia to act on one another. One can proceed in such a way that phosgene and ammonia are first combined to form ela, rnsto # ffe, lilorid and this is then brought to act on triehloroethyl alcohol.
You can also first let phosgene act on trichloroethyl alcohol and then react the product with ammonia, 1-. <I> Example<B>1:</B> </I> To dissolve trieliloroethlyl alcohol in anhydrous ether, add the equimolecular amount of urea sensoride, which is also dissolved in anhydrous ether.
After standing overnight, the ether is distilled off from the possibly filtered solution and the residue is purified by dissolving from petroleum ether.
The transfer takes place. the reaction equation: <B> 1. </B> CCI, -CII, 011 + CI-CONH, = CCI, -CH, 0-CONH, + HCI. In this way, idas urethane, trichloroethyl alcohol, is obtained in thin white needles with a melting point of 64 to 65 '. It is easily soluble in alcohol and ether. It <B> dissolves </B> about <B> 1 </B>? 7o in water at room temperature.
<I> Example 2: </I> A molecule is added to a mixture of molecular quantities of trieliloroethyl alcohol and quinoline in a benzene solution
EMI0002.0001
Phosgene <SEP> dissolved in <SEP> benzene <SEP> <SEP> after <SEP> and <SEP> after <SEP>.
<tb> Well, ch <SEP> <SEP> standing for several days <SEP> becomes <SEP> ice water
<tb> added <SEP> and <SEP> the <SEP> quinoline <SEP> with <SEP> strongly <SEP> diluted <SEP> hydrochloric acid <SEP> shaken out.
<SEP> The <SEP> over
<tb> Chlorcalaium <SEP> dried <SEP> solution, <SEP> die <SEP> das
<tb> contains chlorine carbonate <SEP> of the <SEP> trichloroethyl alcohol <SEP>, <SEP> delivers <SEP> with <SEP> the <SEP> conversion <SEP> with <SEP> ammonia <SEP> also <SEP> the <SEP> described in <SEP> example <SEP> <B> 1 </B> <SEP>
<tb> Urethane, <SEP> which <SEP> insulates <SEP> in <SEP> the usual <SEP> way <SEP>
<tb> and <SEP> are cleaned <SEP>.
<tb>
The <SEP> transfer <SEP> takes place <SEP> <SEP> after <SEP> the
<tb> Reaction equations 2a) <SEP> cc12-CH2OH + Coc12 =
<tb> cci #, -CH, -0-COCI + IICI;
<tb> <B> 2b) <SEP> CCI = CHIO-COCI + NH3 = </B>
<tb> <B> CCI.-CH2O-CONH2 + HCI. </B>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE98666X | 1920-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH98666A true CH98666A (en) | 1923-04-02 |
Family
ID=5646854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH98666D CH98666A (en) | 1920-09-13 | 1921-07-21 | Process for the preparation of a therapeutically valuable ester from trichloroethyl alcohol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH98666A (en) |
-
1921
- 1921-07-21 CH CH98666D patent/CH98666A/en unknown
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