CH311601A - Process for the preparation of a new carbamic acid ester. - Google Patents
Process for the preparation of a new carbamic acid ester.Info
- Publication number
- CH311601A CH311601A CH311601DA CH311601A CH 311601 A CH311601 A CH 311601A CH 311601D A CH311601D A CH 311601DA CH 311601 A CH311601 A CH 311601A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid ester
- carbinol
- ethynyl
- new
- carbamic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- PUNRPAWKFTXZIW-UHFFFAOYSA-N 3-ethylpent-1-yn-3-ol Chemical compound CCC(O)(CC)C#C PUNRPAWKFTXZIW-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000932 sedative agent Substances 0.000 claims description 8
- 230000001624 sedative effect Effects 0.000 claims description 8
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- -1 N-methylcarbamic acid ester Chemical class 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 230000003533 narcotic effect Effects 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000012230 colorless oil Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 2
- 230000000630 rising effect Effects 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Carbaminsäureesters.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Carbaminsäureesters, welches dadurch gekennzeichnet ist, dass man n ¯thinyl-di-Ïthyl-carbinol mit Methylisocyanat umsetzt.
Der a. ls farbloses 61 erhaltene N-Methyl- carbaminsaureester des Athinyl-di-athyl-carbi- nols der Formel
EMI1.1
vom Kp. 84-850 bei 0, 3 mm/Hg ist neu.
Der neue Carbaminsäureester besitzt seda tive und narkotische Wirkung und kann als Beruhigungs- oder Schlafmittel Verwendung finden.
Beispiel :
14,1 Gewichtsteile Methylisocyanat werden unter Feuchtigkeitsausschlu¯ tropfenweise zu 51, 3 Gewichtsteilen Athinyl-di-äthyl-carbinol getropft. Die Temperatur steigt da. bei auf 41 .
Nach Kuhlen auf Raumtemperatur und Stehen iiber Nacht werden 1, 5 Gewiehtsteile wasserfreies Kaliumacetat und 4 Volumteile Tri äthylamin zugegeben, wobei die Temperatur wiederum kurz auf 30 ansteigt. Nach 10 tagigem Stehen bei Raumtemperatur ist der Geruch nach Isocyanat verschwunden.
Das Beaktionsprodukt wird dann in Äther aufgenommen, zweimal mit wenig Wasser, dreimal mit verdünnter Salzsäure und noeh- mals mit Wasser gewaschen, mit Natriumsulfat getroeknet und der ¯ther abdestilliert.
Im Wasserstrahlvakuum wird nun das tuber- schüssige Äthinylcarbinol abdestilliert und der Rüekstand im Hochvakuum destilliert. Der N-Methyl-carbaminsäureester des Äthinyl-di- äthyl-earbinols der Formel
EMI1.2
siedet bei, 84-85¯/0, 3 mm Hg ; er ist ein farbloses 61.
PATENTANSPRUCH:
Verfahren zur Herstellung eines neuen Carbaminsä. ureesters, dadurch gekennzeichnet, dass man Äthinyl-di-äthyl-carbinol mit Methylisocyanat umsetzt.
Der als farbloses Öl erhaltene N-Methyl- carbaminsäureester des Äthinyl-di-äthyl-carbi- nols der Formel
EMI1.3
vom Kp. 84--85 bei 0, 3 mmlHg ist neu.
Der neue CarbaminsÏureester besitzt seda- tive vnd narkotische Wirkung und kann als Beruhigungs-oder Schlafmittel Verwendung finden.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of a new carbamic acid ester.
The subject of the present patent is a process for the production of a carbamic acid ester, which is characterized in that n-thynyl-di-ethyl-carbinol is reacted with methyl isocyanate.
The a. N-methylcarbamic acid ester of ethynyl-diethyl-carbinol of the formula obtained as colorless 61
EMI1.1
from bp 84-850 at 0.3 mm / Hg is new.
The new carbamic acid ester has sedative and narcotic effects and can be used as a sedative or sleeping aid.
Example:
14.1 parts by weight of methyl isocyanate are added dropwise to 51.3 parts by weight of ethynyl-di-ethyl-carbinol with exclusion of moisture. The temperature rises there. at on 41.
After cooling to room temperature and standing overnight, 1.5 parts by weight of anhydrous potassium acetate and 4 parts by volume of triethylamine are added, the temperature again rising briefly to 30. After standing for 10 days at room temperature, the odor of isocyanate has disappeared.
The reaction product is then taken up in ether, washed twice with a little water, three times with dilute hydrochloric acid and once more with water, dried with sodium sulphate and the ether is distilled off.
The excess ethynyl carbinol is then distilled off in a water jet vacuum and the residue is distilled in a high vacuum. The N-methyl-carbamic acid ester of ethynyl-diethyl-earbinol of the formula
EMI1.2
boils at .84-85¯ / 0.3 mm Hg; he is a colorless 61.
PATENT CLAIM:
Process for the preparation of a new carbamine. ureesters, characterized in that ethynyl-di-ethyl-carbinol is reacted with methyl isocyanate.
The N-methylcarbamic acid ester of ethynyl-di-ethyl-carbinol of the formula, obtained as a colorless oil
EMI1.3
from bp 84-85 at 0.3 mmHg is new.
The new carbamic acid ester has a sedative and narcotic effect and can be used as a sedative or sleeping aid.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311601T | 1952-02-22 | ||
| CH307797T | 1955-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311601A true CH311601A (en) | 1955-11-30 |
Family
ID=25735333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311601D CH311601A (en) | 1952-02-22 | 1952-02-22 | Process for the preparation of a new carbamic acid ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311601A (en) |
-
1952
- 1952-02-22 CH CH311601D patent/CH311601A/en unknown
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