AT133155B - Process for the preparation of carbamic acid esters. - Google Patents
Process for the preparation of carbamic acid esters.Info
- Publication number
- AT133155B AT133155B AT133155DA AT133155B AT 133155 B AT133155 B AT 133155B AT 133155D A AT133155D A AT 133155DA AT 133155 B AT133155 B AT 133155B
- Authority
- AT
- Austria
- Prior art keywords
- carbamic acid
- preparation
- acid esters
- heterocyclic
- aromatic
- Prior art date
Links
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 3
- -1 aralkylamine radical Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000001714 carbamic acid halides Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- FWNHTEHWJKUVPG-UHFFFAOYSA-N [3-(dimethylamino)phenyl] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=CC(N(C)C)=C1 FWNHTEHWJKUVPG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Carbaminsäureestern.
EMI1.1
<Desc/Clms Page number 2>
Dimethylcarbaminsäurechlorid in Benzol zwei Stunden auf dem Dampfbad erhitzt. Die Benzol- losung wird dann mit Wasser und Natronlauge gewaschen und im Vakuum destilliert. Der erhaltene Dimethylcarbaminsäureester des 8-Oxvehinolins schmilzt nach dem Umkristallisieren aus Äther bei 80 und bildet ein bei 195 schmelzendes Hydrochlorid.
Beispiel 4 : Eine Lösung von 103 Gewichtsteilen 3-Dimethylaminophenol und 30 Gewichtsteilen Natriumhydroxyd in 250 Teilen Wasser wird auf dem Dampfbad bei 15/lHII Druck eingedampft. Der Rückstand wird in eine Lösung von 75 Gewichtsteilen Dimethylcarbaminsäurechlorid in 200 Teilen Benzol unter Schütteln eingetragen. Zum Schluss wird das Gemisch noch zwei Stunden unter Rückfluss auf dem Dampfbad erhitzt. Hierauf wird das ausgeschiedene Kochsalz in Wasser aufgenommen, die Benzolschicht nochmals mit Natronlauge und Wasser gewaschen. das Lösungsmittel abdestilliert und der Rückstand der Vakuumdestillation unterworfen. Man erhält ungefähr 100 Gewichtsteile Dimethylcarbaminsäure-[3-dimethylaminophenyl]-ester als farbloses Öl vom Kp15 = 190 . Mit Dimethylsulfat bildet dieser Ester eine bei 143 schmelzende quartäre Verbindung.
<Desc / Clms Page number 1>
Process for the preparation of carbamic acid esters.
EMI1.1
<Desc / Clms Page number 2>
Dimethylcarbamic acid chloride in benzene heated on the steam bath for two hours. The benzene solution is then washed with water and sodium hydroxide solution and distilled in vacuo. The dimethylcarbamic acid ester of 8-oxvehinoline obtained melts at 80 after recrystallization from ether and forms a hydrochloride which melts at 195.
Example 4: A solution of 103 parts by weight of 3-dimethylaminophenol and 30 parts by weight of sodium hydroxide in 250 parts of water is evaporated on a steam bath at a pressure of 15/1. The residue is introduced into a solution of 75 parts by weight of dimethylcarbamic acid chloride in 200 parts of benzene with shaking. Finally, the mixture is refluxed on the steam bath for a further two hours. The precipitated common salt is then taken up in water, and the benzene layer is washed again with sodium hydroxide solution and water. the solvent is distilled off and the residue is subjected to vacuum distillation. About 100 parts by weight of dimethylcarbamic acid [3-dimethylaminophenyl] ester are obtained as a colorless oil with a boiling point of 190. With dimethyl sulfate this ester forms a quaternary compound which melts at 143.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE133155X | 1931-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT133155B true AT133155B (en) | 1933-05-10 |
Family
ID=5664848
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT133155D AT133155B (en) | 1931-01-02 | 1931-03-21 | Process for the preparation of carbamic acid esters. |
| AT156371D AT156371B (en) | 1931-01-02 | 1938-03-24 | Process for the preparation of carbamic acid esters. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT156371D AT156371B (en) | 1931-01-02 | 1938-03-24 | Process for the preparation of carbamic acid esters. |
Country Status (1)
| Country | Link |
|---|---|
| AT (2) | AT133155B (en) |
-
1931
- 1931-03-21 AT AT133155D patent/AT133155B/en active
-
1938
- 1938-03-24 AT AT156371D patent/AT156371B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT156371B (en) | 1939-06-26 |
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