CH284072A - Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine. - Google Patents
Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine.Info
- Publication number
- CH284072A CH284072A CH284072DA CH284072A CH 284072 A CH284072 A CH 284072A CH 284072D A CH284072D A CH 284072DA CH 284072 A CH284072 A CH 284072A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- thiazolidine
- imino
- dimethyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- GMFUTRCIEWHKBH-UHFFFAOYSA-N 3,4-dimethyl-5-phenyl-1,3-thiazolidin-2-imine Chemical compound S1C(=N)N(C)C(C)C1C1=CC=CC=C1 GMFUTRCIEWHKBH-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 230000036826 Excretion Effects 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N Rhodanine Chemical class O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 dimethylphenyliminothiazolidine Chemical compound 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
Description
Verfahren zur Herstellung von 3,4-Dimethyl-5-phenyl-2-imino-thiazolidin. In der Schweiz. Patentschrift Nr.266997 ist ein Verfahren zur Herstellung von 3,4-Di- methyl-5-phenyl-2-imino-thiazolidin beschrie ben, welches dadurch gekennzeichnet ist, dass man ein 1-Phen@>1-1-halogen-2-methylamino- propanhy drohalogenid mit einem Salz der Thioeyansäure in CTegenwart eines Lösungs mittels umsetzt.
Es wurde nun gefunden, dass man 3,4-Di- methyl-5-phenyl-2-imino-thiazolidin auch da durch herstellen kann, dass man 1-Phenyl-l- rhodan - 2 - metliy 1a minopropan-hydrorhodanid in Gegenwart eines Lösungsmittels, zweck mässig im alkalischen -Medium, erwärmt.
1-Phenyl-l -rhodan-2-methylaminopropanhydro- rhodanid wird erhalten durch Erwärmen von -Phenyl-l-halogen-2-methyl-aminopropan-hy- drohalogenid mit einem Salz der Thiocyan- säure in saurem Medium bei pH 1 bis 2,5.
Die Umlagerungsreaktion kann sowohl in Wasser unter zweckmässiger Zugabe von wenig Alkalilauge als auch in einem organischen Lösungsmittel, wie Methanol, Äthanol, Butyl- äther oder Benzol, unter zweckmässiger Zugabe eines alkalischen Mittels durchgeführt werden.
Das Verfahrensprodukt soll als Arzneimit tel sowie als Zwischenprodukt bei der Her stellung von Arzneimitteln Verwendung fin den. <I>Beispiel:</I> 26,6 g 1-Phenyl.-1-rhodan-2-methylamino- propan-hydrorhodanid werden in 150 ein- Wasser unter Erwärmen gelöst und mit 5 em3 konzentrierter Natronlauge versetzt, worauf alsbald die kristalline Ausscheidung von Dimethylphenyliminothiazolidinhydrorho- danid beginnt, F. 190 bis 192 . Ausbeute: 23,5 g = 88 @/o d. Th.
Aus der Lösung des rhodanwasserstoffsau- ren Salzes in Wasser wird die Base durch Zugabe von Alkali ausgefällt. Durch Aufneh men des öl.s in Alkohol, Trocknen der Lösung und Zugabe von alkoholischer Salzsäure wird die Base in das Hydrochlorid vom F. 222 bis 224 übergeführt.
Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine. In Switzerland. Patent No. 266997 describes a process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine, which is characterized in that a 1-Phen @> 1-1-halogen-2 -methylamino-propanhy drohalide with a salt of thioeyanoic acid in the presence of a solvent.
It has now been found that 3,4-dimethyl-5-phenyl-2-imino-thiazolidine can also be prepared by making 1-phenyl-1-rhodan - 2 - metliy 1a minopropane hydrorhodanide in the presence of a Solvent, expediently in an alkaline medium, heated.
1-phenyl-1-rhodan-2-methylaminopropanhydrhodanide is obtained by heating -phenyl-1-halogen-2-methyl-aminopropane-hydrohalide with a salt of thiocyanoic acid in an acidic medium at pH 1 to 2, 5.
The rearrangement reaction can be carried out either in water with the appropriate addition of a little alkali or in an organic solvent such as methanol, ethanol, butyl ether or benzene, with the appropriate addition of an alkaline agent.
The process product is intended to be used as a drug and as an intermediate in the manufacture of drugs. <I> Example: </I> 26.6 g of 1-phenyl.-1-rhodane-2-methylamino-propane-hydrorhodanide are dissolved in 150 one-liter water with heating and mixed with 5 cubic meters of concentrated sodium hydroxide solution, whereupon the crystalline Excretion of dimethylphenyliminothiazolidine hydrorho- danide begins, F. 190 to 192. Yield: 23.5 g = 88% / o d. Th.
The base is precipitated from the solution of the rhodanic acid salt in water by adding alkali. By taking up the oil in alcohol, drying the solution and adding alcoholic hydrochloric acid, the base is converted into the hydrochloride with a melting point of 222 to 224.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284072T | 1950-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH284072A true CH284072A (en) | 1952-07-15 |
Family
ID=4484369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH284072D CH284072A (en) | 1950-02-09 | 1950-02-09 | Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH284072A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE942027C (en) * | 1954-08-11 | 1956-04-26 | Knoll Ag | Process for the preparation of substituted 2-iminothiazolidines |
-
1950
- 1950-02-09 CH CH284072D patent/CH284072A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE942027C (en) * | 1954-08-11 | 1956-04-26 | Knoll Ag | Process for the preparation of substituted 2-iminothiazolidines |
| DE944551C (en) * | 1954-08-11 | 1956-06-21 | Knoll Ag | Process for the preparation of substituted 2-iminothiazolidines |
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