CH281960A - Process for the preparation of a heterocyclic carbamic acid derivative. - Google Patents
Process for the preparation of a heterocyclic carbamic acid derivative.Info
- Publication number
- CH281960A CH281960A CH281960DA CH281960A CH 281960 A CH281960 A CH 281960A CH 281960D A CH281960D A CH 281960DA CH 281960 A CH281960 A CH 281960A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid derivative
- carbamic acid
- preparation
- heterocyclic
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- -1 heterocyclic carbamic acid derivative Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung eines beterocyclischen Carbaminsäurederivates. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines heterocycli- sehen Carbaminsäurederivates. Das Verfahren ist dadurch gekennzeiehnet, dass man eine Verbindunz der Formel
EMI0001.0008
mit einem Carbaminsäurederivat der Formel
EMI0001.0010
umsetzt, worin X und Y zwei sich im Verlaufe des Verfahrens abspaltende Reste bedeuten.
Die erhaltene neue Verbindung, das 1-Iso- propy 1- 3 - methyl-1,2,4-triazolyl - (5) - dimethyl- carbamat, siedet unter 13 mm Druck bei 127 bis 131 . Sie soll als Wirkstoff für Sehgd- lingsbekämpfungsmittel Verwendung finden.
<I>Beispiel:</I> 12 Teile 1-Isopropyl-3-methyl-1,2,4-triazo- lon-(5) werden mit 7 Teilen Kaliumcarbonat und 200 Teilen Benzol an einem Rückfluss- kühler mit -Wasserabscheider so lange erhitzt, bis kein Wasser mehr übergeht. Dann kühlt man das Reaktionsgemiseh etwas ab und gibt 72 Teile Dimethylcarbaminsäureehlorid hinzu.
Durch Erhitzen am Rüekfliass über Nacht wird die Reaktion vervollständigt. Um eventuell nicht umgesetztes Triazolon zu entfernen, wird die erkaltete benzolische Lösung mit Ka- liumearbonatlösung durchgerührt, die ben- zolische Schicht. abgehoben, mit. Wasser neu tralgewaschen und getrocknet. Nach Entfer nen des Lösungsmittels wird der Rüekstand durch Destillation im Hochvakuum gereinigt..
Das 1- Isopropyl - 3 - methyl-1,2,4-triazolyl- (5) - dimethylcarbamat siedet. unter 13 mm Druck bei 127 bis 131<B>0</B>.
Process for the preparation of a beterocyclic carbamic acid derivative. The present patent is a process for the preparation of a heterocyclic carbamic acid derivative see. The process is characterized in that it is a compound of the formula
EMI0001.0008
with a carbamic acid derivative of the formula
EMI0001.0010
converts, where X and Y are two radicals split off in the course of the process.
The new compound obtained, 1-isopropy1-3-methyl-1,2,4-triazolyl- (5) -dimethylcarbamate, boils at 127 to 131 under 13 mm pressure. It should be used as an active ingredient for anti-sighting agents.
<I> Example: </I> 12 parts of 1-isopropyl-3-methyl-1,2,4-triazolone (5) are mixed with 7 parts of potassium carbonate and 200 parts of benzene in a reflux condenser with a water separator Heated for a long time until no more water passes over. The reaction mixture is then cooled somewhat and 72 parts of dimethylcarbamic acid chloride are added.
The reaction is completed by heating on the back flask overnight. In order to remove any unreacted triazolone, the cooled benzene solution is stirred with potassium carbonate solution, the benzene layer. lifted, with. Water newly tralwashed and dried. After removing the solvent, the residue is purified by distillation in a high vacuum.
The 1-isopropyl-3-methyl-1,2,4-triazolyl- (5) -dimethylcarbamate is boiling. under 13 mm pressure at 127 to 131 <B> 0 </B>.
Claims (1)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2681879X | 1949-08-22 | ||
| CH2681916X | 1949-08-22 | ||
| CH2681914X | 1949-08-22 | ||
| CH2681915X | 1949-08-22 | ||
| CH2694712X | 1949-08-22 | ||
| CH281960T | 1949-08-26 | ||
| GB3001049A GB681376A (en) | 1949-11-23 | 1949-11-23 | Manufacture of heterocyclic carbamic acid derivatives and their use as agents for combating pests |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH281960A true CH281960A (en) | 1952-03-31 |
Family
ID=32303878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH281960D CH281960A (en) | 1949-08-22 | 1949-08-26 | Process for the preparation of a heterocyclic carbamic acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH281960A (en) |
-
1949
- 1949-08-26 CH CH281960D patent/CH281960A/en unknown
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