CH235237A - Process for the preparation of 2 ', 3', 5'-trimethyl-cyclopentane-1 ', 5-spiro-1-methyl-2,4,6-triketo-hexahydropyrimidine. - Google Patents
Process for the preparation of 2 ', 3', 5'-trimethyl-cyclopentane-1 ', 5-spiro-1-methyl-2,4,6-triketo-hexahydropyrimidine.Info
- Publication number
- CH235237A CH235237A CH235237DA CH235237A CH 235237 A CH235237 A CH 235237A CH 235237D A CH235237D A CH 235237DA CH 235237 A CH235237 A CH 235237A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- cyclopentane
- triketo
- methyl
- trimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PNUFYSGVPVMNRN-UHFFFAOYSA-N 1,2,4-trimethylcyclopentane Chemical compound CC1CC(C)C(C)C1 PNUFYSGVPVMNRN-UHFFFAOYSA-N 0.000 claims 1
- AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003533 narcotic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000001916 dieting Nutrition 0.000 description 1
- 230000037228 dieting effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 2',3',5'-Trimethyl-cyclopentau-1',5-spiro-l-methyl- 2,4,6-triketo-hegahydropyrimidin.
EMI0001.0004
Gegenstand <SEP> vorliegenden <SEP> Zusatzpatentes
<tb> ist <SEP> ein <SEP> Verfahren <SEP> zur <SEP> Herstellung <SEP> von
<tb> 2', <SEP> 3', <SEP> 5' <SEP> - <SEP> Trnmethyl <SEP> - <SEP> cyclio,pentan1-1', <SEP> 5 <SEP> - <SEP> sipiro <SEP> -1 methyl <SEP> - <SEP> 2,4,6 <SEP> - <SEP> triketo <SEP> - <SEP> hexahydropyrimidin,
<tb> welches <SEP> dadurch <SEP> gekennz@eiehniet <SEP> ist, <SEP> dass <SEP> man
<tb> 2,3,5-Tritm!ethyl-cycliopentan-l-cya.n-l-,carbon ssäureester <SEP> mit <SEP> Dii.cyandiamid <SEP> kondensiert,
<SEP> das
<tb> Kondensiationsprodukt <SEP> methyliert <SEP> und <SEP> an schliessend <SEP> der <SEP> I-Iydtrolys,e <SEP> unterwirft.
<tb>
Dia <SEP> neue <SEP> Verbindung <SEP> ist <SEP> ein <SEP> hochviskoses,
<tb> schwach <SEP> gelblich <SEP> gefärbtes <SEP> 01, <SEP> Kp. <SEP> p,4 <SEP> 139 <SEP> bis
<tb> 141 . <SEP> Sie <SEP> besitzt <SEP> na.rkotn)s,che <SEP> -Wirkung.
<tb>
<I>Beispiel:</I>
<tb> Zu <SEP> einer <SEP> Lösung <SEP> von <SEP> 4,6 <SEP> Teilen <SEP> Natrium
<tb> in <SEP> 70 <SEP> Teilen <SEP> absolutem <SEP> Alkohol <SEP> fügt <SEP> man
<tb> <B>20,9</B> <SEP> Teile <SEP> 2, <SEP> 3, <SEP> 5 <SEP> - <SEP> Trimetliyl <SEP> - <SEP> cyelop <SEP> entan <SEP> -1 cyan-l-.ca,rbunLäureäthylestp-,r <SEP> und <SEP> 10 <SEP> Teile
<tb> Dicya-näiamid <SEP> und <SEP> erhitzt <SEP> 10 <SEP> Stunden <SEP> lang
<tb> unten <SEP> Rückflsusslkühl!un#g. <SEP> Naaob:
<SEP> dem <SEP> Erkalten
<tb> gibt <SEP> man <SEP> tropfenweise <SEP> 12,6 <SEP> Teile <SEP> Dimetliyl sufat <SEP> hinzu, <SEP> wobei <SEP> man <SEP> durch <SEP> Kühlung <SEP> die
<tb> Temperatur <SEP> unterhalb <SEP> 50 <SEP> hälit. <SEP> Hierauf ,destilliert man den Alkohol ab und erbnitzt !den Rückstand mit dem sechsfachen Menge Schwefelsäure (25%ig)
8 Stunden lang zum Sieden. Die neue Verbindung läss t sieh nricht in kristallisierter Form erhalten, sie wded durch Ausiäthern iss,okert und nach leim Trocknen über entwässertem Natriumsulfat und Verjagen des Äthers im Vakuum destilliert.
Process for the preparation of 2 ', 3', 5'-trimethyl-cyclopentau-1 ', 5-spiro-1-methyl-2,4,6-triketo-hegahydropyrimidine.
EMI0001.0004
Subject <SEP> of the present <SEP> additional patent
<tb> <SEP> is a <SEP> process <SEP> for <SEP> production <SEP> of
<tb> 2 ', <SEP> 3', <SEP> 5 '<SEP> - <SEP> Trnmethyl <SEP> - <SEP> cyclio, pentane1-1', <SEP> 5 <SEP> - <SEP> sipiro <SEP> -1 methyl <SEP> - <SEP> 2,4,6 <SEP> - <SEP> triketo <SEP> - <SEP> hexahydropyrimidine,
<tb> which <SEP> is marked with <SEP> @ eiehniet <SEP>, <SEP> that <SEP> man
<tb> 2,3,5-Tritm! ethyl-cycliopentane-l-cya.n-l-, carboxylic acid ester <SEP> condensed with <SEP> di.cyandiamide <SEP>,
<SEP> that
<tb> Condensation product <SEP> methylates <SEP> and <SEP> followed by <SEP> which subjects <SEP> Iydtrolys, e <SEP>.
<tb>
The <SEP> new <SEP> connection <SEP> is <SEP> a <SEP> highly viscous,
<tb> weak <SEP> yellowish <SEP> colored <SEP> 01, <SEP> Kp. <SEP> p, 4 <SEP> 139 <SEP> to
<tb> 141. <SEP> You <SEP> has <SEP> na.rkotn) s, che <SEP> effect.
<tb>
<I> Example: </I>
<tb> To <SEP> a <SEP> solution <SEP> of <SEP> 4.6 <SEP> parts <SEP> sodium
<tb> in <SEP> 70 <SEP> parts <SEP> absolute <SEP> alcohol <SEP> adds <SEP> man
<tb> <B> 20,9 </B> <SEP> parts <SEP> 2, <SEP> 3, <SEP> 5 <SEP> - <SEP> Trimetliyl <SEP> - <SEP> cyelop <SEP> entan <SEP> -1 cyan-l-.ca, rbunLäureäthylestp-, r <SEP> and <SEP> 10 <SEP> parts
<tb> Dicya-Näiamid <SEP> and <SEP> heats <SEP> for 10 <SEP> hours <SEP>
<tb> below <SEP> reflux oil cool! un # g. <SEP> Naaob:
<SEP> the <SEP> cooling down
<tb> <SEP> one <SEP> <SEP> drop by drop <SEP> 12.6 <SEP> parts <SEP> Dimethylsufat <SEP>, <SEP> whereby <SEP> one <SEP> by <SEP> cooling <SEP > the
<tb> temperature <SEP> below <SEP> 50 <SEP> holds. <SEP> Then, the alcohol is distilled off and the residue is carved out with six times the amount of sulfuric acid (25%)
Simmer for 8 hours. The new compound cannot be preserved in crystallized form, it is eaten by dieting, okert and after glue drying over dehydrated sodium sulphate and expulsion of the ether, it is distilled in a vacuum.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH235237T | 1942-07-29 | ||
| CH230367T | 1942-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235237A true CH235237A (en) | 1944-11-15 |
Family
ID=25727476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235237D CH235237A (en) | 1942-07-29 | 1942-07-29 | Process for the preparation of 2 ', 3', 5'-trimethyl-cyclopentane-1 ', 5-spiro-1-methyl-2,4,6-triketo-hexahydropyrimidine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH235237A (en) |
-
1942
- 1942-07-29 CH CH235237D patent/CH235237A/en unknown
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