CH228147A - Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid. - Google Patents
Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid.Info
- Publication number
- CH228147A CH228147A CH228147DA CH228147A CH 228147 A CH228147 A CH 228147A CH 228147D A CH228147D A CH 228147DA CH 228147 A CH228147 A CH 228147A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- cycloheptenyl
- barbituric acid
- preparation
- dicyandiamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- -1 cycloheptenyl-methyl-cyanoacetic acid ester Chemical class 0.000 claims description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 235000019658 bitter taste Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
Verfahren zur Darstellung von 5-5-C-C-41-Cycloheptenyl-methyl-N-methyl-barbitursäure. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Herstellung von 5-5-C-C-d1-Cycloheptenyl-methyl-N-me- thyl-barbitursäure, dadurch gekennzeichnet, dass ein dl-Cycloheptenyl-methyl-cyanessig- säureester mit Dicyandiamid kondensiert,
das erhaltene Produkt mit Dimethylsulfat me- thyliert und das als Zwischenprodukt ent stehende Cyan-iminoderivat zur Barbitur- säureverbindung hydrolysiert wird.
<I>Beispiel:</I> 20,7 Teile dl-Cycloheptenyl-methyl-cyan- essigsäuremethylester erhitzt man mit einer Lösung von 4,6 Teilen Natrium in 100 Tei len Methanol unter Zugabe von 9 Teilen Dicy andiamid 8 Stunden auf ca. 70 . Nach dem Erkalten fügt man tropfenweise 24 Teile Dimethylsulfat hinzu, wobei man dafür Sorge trägt, dass die Temperatur nicht über 50 steigt.
Hierauf verjagt man das Methanol im Wasserbade und verkocht den Rückstand mit der zehnfachen Menge<B>25%</B> Schwefelsäure. Die sich abscheidende C-C-Cycloheptenyl- methyl-N-methyl-barbitursäure bildet nach dem Umlösen aus<B>30%</B> Alkohol farblose Prismen vom F. 124 .
Process for the preparation of 5-5-C-C-41-cycloheptenyl-methyl-N-methyl-barbituric acid. The subject of the present additional patent is a process for the production of 5-5-C-C-d1-cycloheptenyl-methyl-N-methyl-barbituric acid, characterized in that a dl-cycloheptenyl-methyl-cyanoacetic acid ester condenses with dicyandiamide,
the product obtained is methylated with dimethyl sulfate and the cyano-imino derivative formed as an intermediate is hydrolyzed to the barbituric acid compound.
<I> Example: </I> 20.7 parts of dl-cycloheptenyl-methyl-cyano-acetic acid methyl ester are heated with a solution of 4.6 parts of sodium in 100 parts of methanol with the addition of 9 parts of dicyandiamide for 8 hours for approx. 70. After cooling, 24 parts of dimethyl sulfate are added dropwise, taking care that the temperature does not rise above 50.
The methanol is then chased away in a water bath and the residue is boiled with ten times the amount <B> 25% </B> sulfuric acid. The C-C-cycloheptenyl-methyl-N-methyl-barbituric acid which separates out forms colorless prisms of F. 124 after dissolving from <B> 30% </B> alcohol.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228147X | 1940-03-09 | ||
| CH224789T | 1941-03-07 | ||
| CH228147T | 1941-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228147A true CH228147A (en) | 1943-07-31 |
Family
ID=27177946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228147D CH228147A (en) | 1940-03-09 | 1941-03-07 | Process for the preparation of 5-5-C-C-1-cycloheptenyl-methyl-N-methyl-barbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228147A (en) |
-
1941
- 1941-03-07 CH CH228147D patent/CH228147A/en unknown
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