DE1695852A1 - Process for the preparation of 3-methyl-5-isopropylphenyl esters - Google Patents
Process for the preparation of 3-methyl-5-isopropylphenyl estersInfo
- Publication number
- DE1695852A1 DE1695852A1 DE19671695852 DE1695852A DE1695852A1 DE 1695852 A1 DE1695852 A1 DE 1695852A1 DE 19671695852 DE19671695852 DE 19671695852 DE 1695852 A DE1695852 A DE 1695852A DE 1695852 A1 DE1695852 A1 DE 1695852A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- isopropylphenyl
- preparation
- esters
- pyrrolidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung von 3-Methyl-5-isoropylphenylestern Im Hauptpatent ........ (Patentanmeldung Sch 38 577 IVd/l2 p) sind Verfahren zur Herstellung von 3-Methyl-5-isopropylphenylestern angegeben worden, die darin bestehen, daß man entweder Chlorameisensäure-3-methyl-5-isopropylphenylester oder ein. in analoger Weise reagierendes funktionelles Derivat der entsprechenden Säure mit Pyrrolidin oder Morpholin gegebenenfalls in Gegenwart eines säurebindenden Mittels umsetzt oder daß man Pyrolidin- bzw. Morpholin-N-carbonsäurechlorid oder ein äquivalent reaktionsfähiges Derivat der entsprechenden Säure mit 3-Methyl-5-isopropylphenol gegebenenfalls in Gegenwart eines säurebindenden Mittels umsetzt. Process for preparing 3-methyl-5-isopropylphenyl esters Im Main patent ........ (patent application Sch 38 577 IVd/l2 p) are manufacturing processes of 3-methyl-5-isopropylphenyl esters, consisting in that one either 3-methyl-5-isopropylphenyl chloroformate or a. in analogue Moderately reacting functional derivative of the corresponding acid with pyrrolidine or morpholine optionally in the presence of an acid-binding agent or that pyrolidine or morpholine-N-carboxylic acid chloride or an equivalent reactive derivative of the corresponding acid with 3-methyl-5-isopropylphenol optionally reacting in the presence of an acid-binding agent.
Die neuen Ester, namentlich der 3-Methyl-5-isopropylphenylester der Pyrrolidin-N-carbonsäure, zeigen sehr gute Wirkungen gegen Dermatophyten. Weiterhin besitzen sie die Wirkung eines"tranquilliser".The new esters, namely the 3-methyl-5-isopropylphenyl ester Pyrrolidine-N-carboxylic acid show very good effects against dermatophytes. Farther they have the effect of a "tranquillizer".
Es wurde nun gefunden. daß man die Verbindunzen der allgemeinen Formel in der R den Pyrrolidino-oder Morpholinorest bedeutet, auch erhalten kann, indem man 3-Methyl-5-isopropyl-phenol und Pyrrolidin bzw. Morpholin mit Phosgen in Gegenwart eines inerten Lösungsmittels bei erhöhter Temperatur umsetzt.It has now been found. that one can combine the compounds of the general formula in which R is the pyrrolidino or morpholino radical, can also be obtained by reacting 3-methyl-5-isopropyl-phenol and pyrrolidine or morpholine with phosgene in the presence of an inert solvent at elevated temperature.
Als inerte Lösungsmittel kommen insbesondere aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Chlorbenzol, in Frage.Inert solvents are, in particular, aromatic hydrocarbons, such as benzene, toluene, chlorobenzene.
Das Phosgen. wird zweckmäßig in die Lösung von 3-Methyl-5-isopropylphenol und Amin eingeleitet.The phosgene. is suitably added to the solution of 3-methyl-5-isopropylphenol and amine initiated.
Beispiel 1 150 g 3-Methyl-5-isopropylphenol und 95 g Pyrrolidin werden mit 1000 ml Benzol unter Rühren und RUckRluß erhitzt und im Verlauf von 4 Stunden 200g Phosgen eingeleitet. Nach AbkUhlen der Lösung wird der Reihe nach mit Eiswasser, verdünnter Salzsäure und NaHOO3-Lösung gewaschen. Nach dem Trocknen über Natriumsulfat wird das Lösungsmittel im Vakuum entfernt und der Rückstand im Vakuum destilliert. Man erhält 165 g (= 67%) Pyrrolidin-N-carbonsäure-3-methyl-5-isopropylphenylester vom Siedepunkt Kp0,09 = l450C.Example 1 150 g of 3-methyl-5-isopropylphenol and 95 g of pyrrolidine heated with 1000 ml of benzene with stirring and reflux and over the course of 4 hours 200g phosgene initiated. After cooling the solution, it is washed in sequence with ice water, diluted hydrochloric acid and NaHOO3 solution. After drying over sodium sulfate the solvent is removed in vacuo and the residue distilled in vacuo. 165 g (=67%) of pyrrolidine-N-carboxylic acid 3-methyl-5-isopropylphenyl ester are obtained from the boiling point Kp0.09 = l450C.
Beispiel 2 150 g 9-Methyl -5-isopropylphenol und 115 g Morpholin werden in 2 1 Chlorbenzol unter Rühren auf 1200C erwärmt und im Verlauf von 4 Stunden 2oog Phosgen eingeleitet. Nach Waschen des Reaktionsgemisches mit Eiswasser, verdünnter Salzsäure und NaHCO3-Lösung wird das Lösungsmittel im Vakuum entfernt und der Rückstand aus Petroläther umkristallisiert. Man erhält 187 g Morpholin-N-carbonsäure-3-methyl-5-isopropylphenylester vom Schme-lzpunkt 520C.Example 2 150 g of 9-methyl-5-isopropylphenol and 115 g of morpholine heated to 120° C. in 2 liters of chlorobenzene with stirring and 2oog over the course of 4 hours phosgene initiated. After washing the reaction mixture with ice water, dilute Hydrochloric acid and NaHCO3 solution, the solvent is removed in vacuo and the residue recrystallized from petroleum ether. 187 g of 3-methyl-5-isopropylphenyl morpholine-N-carboxylate are obtained from melting point 520C.
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC038577 | 1966-03-02 | ||
| DESC041054 | 1967-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695852A1 true DE1695852A1 (en) | 1971-05-13 |
Family
ID=32909376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671695852 Pending DE1695852A1 (en) | 1966-03-02 | 1967-07-21 | Process for the preparation of 3-methyl-5-isopropylphenyl esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1695852A1 (en) |
-
1967
- 1967-07-21 DE DE19671695852 patent/DE1695852A1/en active Pending
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