CH314206A - Process for the preparation of 1-dimethylamino-3- (3'-methoxy-phenyl) -3-thiazolyl- (2 ') -hexanone- (4) - Google Patents
Process for the preparation of 1-dimethylamino-3- (3'-methoxy-phenyl) -3-thiazolyl- (2 ') -hexanone- (4)Info
- Publication number
- CH314206A CH314206A CH314206DA CH314206A CH 314206 A CH314206 A CH 314206A CH 314206D A CH314206D A CH 314206DA CH 314206 A CH314206 A CH 314206A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethylamino
- thiazolyl
- hexanone
- preparation
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- -1 ethylmagnesium halide Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000001582 butter acid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 1-Dimethylamino-3-(3'-methoxy-phenyl)-3-thiazolyl- (2')-hexanon-(4) Gegenstand der vorliegenden Erfindung ist. ein Verfahren zur Herstellung von 1-Di methylamino-3-(3'-methoxy-phenyl)-3-thiazolyl- (2')-hexanon #-(4), welches dadurch gekenn zeichnet ist, da.ss man .einen a-(3-Methoxy- phenyl;
)-a-thiazolyl-(2) -y-dimethylamino-but- tersäureester mit einem Äthylmagnesiumhalo- genid umsetzt.
Die erhaltene Base lässt sieh mit Malein- säure in das entsprechende Salz überführen. welches in Form kleiner farbloser Nadeln an fällt und einen Schmelzpunkt von l23-125 aufweist. Die Base, insbesondere deren lös liches Maleinat, findet als Arzneimittel Ver wendung.
<I>Beispiel</I> 51 Gewichtsteile (3-Methoxy-phenyl)-thiazo- lyl-(2)-essigsä.uremethylester, 22 Gewichtsteile Dimethylaminoäthylchlorid, 8,5 Gewichtsteile Natriuma.mid und 200 Gewichtsteile Toluol werden 30 Minuten bei 35 gerührt und an schliessend 2 Stunden unter Rückfluss gekocht. ES wird wieder gekühlt, 200 Gewichtsteile Wasser zum Reaktionsprodukt gegeben und die Toluollösung abgetrennt.
Beim Aufarbei ten dieser Lösung werden 53 Gewichtsteile des a-(3-Methoxy-phenyl) -a-thiazolyl-(2)-y-dime- thylamino-buttersäuremethylesters erhalten.
Dieser rohe Ester wird in 100 Gewichts teilen Benzol gelöst und bei 25-30 zu einer Organomagnesiumlösung getropft, die aus 7,7 Gewichtsteilen Magnesitunspänen, 35 Ge- wichtsteilen Äthylbromid und 100 Gewichts teilen Äther bereitet war. Es wird eine Stunde auf 50-55 nacherwärmt und dann in der üblichen Weise mit Ammonehloridlösung zer setzt.
Beim Eindampfen der organischen Lö sung werden 48,5 Gewichtsteile eines roten Öls erhalten, welches das 1-Dimethylamino-3-(3'- methoxy-phenyl)-3-thiazolyl-(2')-hexanon- (4) darstellt. Das basische Keton ist ein gelbes, stark viskoses Öl vom Kp-0,6 175-180 .
Das Maleinat ist sehr kristallisationsfreu- dig und kristallisiert aus Essigester in kleinen farblosen Nadeln vom Schmelzpunkt 123 bis 125 . Die Base hat die Formel:
EMI0001.0059
Durch Kochen mit 48 o/oiger Bromwasser stoffsäure lässt sich die Äthergruppe im Mole kül aufsprengen, wobei das 1-Dimethylamino- 3-(3'-oxy-phenyl)-3-thiazolyl-(2')-hexanon-(4) entsteht.
Aus Essigester kristallisiert dieses in farblosen Nadeln vom Schmelzpunkt 113 bis 115 .
Process for the preparation of 1-dimethylamino-3- (3'-methoxyphenyl) -3-thiazolyl- (2 ') -hexanone- (4) is the subject of the present invention. a process for the preparation of 1-dimethylamino-3- (3'-methoxyphenyl) -3-thiazolyl- (2 ') - hexanone # - (4), which is characterized in that one .ein a - (3-methoxyphenyl;
) -a-thiazolyl- (2) -y-dimethylamino-but- ter acid ester is reacted with an ethylmagnesium halide.
The base obtained can be converted into the corresponding salt with maleic acid. which falls in the form of small colorless needles and has a melting point of 123-125. The base, especially its soluble maleate, is used as a drug.
<I> Example </I> 51 parts by weight of (3-methoxyphenyl) -thiazo- lyl- (2) -acetic acid methyl ester, 22 parts by weight of dimethylaminoethyl chloride, 8.5 parts by weight of sodium amide and 200 parts by weight of toluene are 30 minutes at 35 stirred and then refluxed for 2 hours. It is cooled again, 200 parts by weight of water are added to the reaction product and the toluene solution is separated off.
When working up this solution, 53 parts by weight of a- (3-methoxyphenyl) -a-thiazolyl- (2) -y-dimethylamino-butyric acid methyl ester are obtained.
This crude ester is dissolved in 100 parts by weight of benzene and added dropwise at 25-30 to an organomagnesium solution which was prepared from 7.7 parts by weight of magnesite shavings, 35 parts by weight of ethyl bromide and 100 parts by weight of ether. It is heated to 50-55 for an hour and then zer sets in the usual way with ammonium chloride solution.
When the organic solution is evaporated, 48.5 parts by weight of a red oil are obtained, which is 1-dimethylamino-3- (3'-methoxyphenyl) -3-thiazolyl- (2 ') -hexanone- (4). The basic ketone is a yellow, highly viscous oil with a boiling point of 0.6 175-180.
The maleate is very easy to crystallize and crystallizes from ethyl acetate in small, colorless needles with a melting point of 123 to 125. The base has the formula:
EMI0001.0059
The ether group in the molecule can be broken up by boiling with 48% hydrobromic acid, whereby 1-dimethylamino-3- (3'-oxy-phenyl) -3-thiazolyl- (2 ') -hexanone- (4) is formed .
This crystallizes from ethyl acetate in colorless needles with a melting point of 113 to 115.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE314206X | 1951-02-08 | ||
| CH305886T | 1952-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314206A true CH314206A (en) | 1956-05-31 |
Family
ID=25735015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314206D CH314206A (en) | 1951-02-08 | 1952-01-24 | Process for the preparation of 1-dimethylamino-3- (3'-methoxy-phenyl) -3-thiazolyl- (2 ') -hexanone- (4) |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314206A (en) |
-
1952
- 1952-01-24 CH CH314206D patent/CH314206A/en unknown
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