CH235231A - Process for the preparation of 3'-methyl-cyclopentane-1 ', 5-spiro-1-methyl-2,4,6-triketo-hexahydropyrimidine. - Google Patents
Process for the preparation of 3'-methyl-cyclopentane-1 ', 5-spiro-1-methyl-2,4,6-triketo-hexahydropyrimidine.Info
- Publication number
- CH235231A CH235231A CH235231DA CH235231A CH 235231 A CH235231 A CH 235231A CH 235231D A CH235231D A CH 235231DA CH 235231 A CH235231 A CH 235231A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- methyl
- cyclopentane
- triketo
- spiro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000003533 narcotic effect Effects 0.000 claims description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
EMI0001.0001
Verfahren <SEP> zur <SEP> Herstellung <SEP> von <SEP> 3'-1Vlethyl-cyclopentau-1',5-spiro-l-methyl 2,4,6-tr <SEP> iketo-hexahydr <SEP> opyrimi <SEP> din.
EMI0001.0002
Gegenstand <SEP> vorliegenden <SEP> Zusatzpatentes
<tb> ist <SEP> ein <SEP> Verfahren <SEP> zur <SEP> Herstellung <SEP> von
<tb> 3'- <SEP> Methyl.- <SEP> cyclopentan <SEP> -1',5 <SEP> -spiro-1-methyl 2,4,6,=triketa-hexa@hyd@ropyrimidin, <SEP> welches. <SEP> da durch <SEP> gekennzeichnet <SEP> ist., <SEP> dass <SEP> man <SEP> 3-Methyl cycl'o#pentan-1-cyan-1--ca,rbon <SEP> ,säureesiter <SEP> mit
<tb> Methylharnstaff <SEP> kondensiert <SEP> und <SEP> das <SEP> erhal teno <SEP> Produkt <SEP> anschliessend <SEP> der <SEP> HydTolyse
<tb> unterwirft.
<tb>
Das <SEP> neue <SEP> Produkt <SEP> bildet <SEP> farblose <SEP> Nadeln
<tb> vom <SEP> F. <SEP> 113-114 <SEP> u,nd <SEP> besitzt <SEP> narkotische
<tb> Wirkung.
<tb>
<I>Beispiel:</I>
<tb> Zu <SEP> einer <SEP> Lösung <SEP> von <SEP> 4,6 <SEP> Teilen <SEP> Natriurn metall <SEP> in <SEP> 100 <SEP> Volumtei.len <SEP> absolutem <SEP> Me t:hanol <SEP> fügt <SEP> man <SEP> 18,3 <SEP> Teile <SEP> 3-Methyl-cyclo, pentan-l-cyan-l-carbon3äureäthylester <SEP> und
<tb> 8 <SEP> Teile <SEP> Methyl#harnstoff <SEP> und <SEP> erhitzt <SEP> 10 <SEP> Stun den <SEP> unter <SEP> Rückfluss.
<SEP> Nach <SEP> dem <SEP> Abdestillie- ren des Methanols verkocht man den Rück stand w ähTend 8 Stunden mit der seehsf achen Menge Schwefelsäure (2.5<B>%).</B> Nach dem Er kalten trennt man das rohe Produkt von un verändertem Ester und kristallisiert aus ver dünntem Methanol um. Das reine P'roldukt weist einen Schmelzpunkt von 113-114 auf.
EMI0001.0001
Process <SEP> for <SEP> production <SEP> of <SEP> 3'-1Vlethyl-cyclopentau-1 ', 5-spiro-1-methyl 2,4,6-tr <SEP> iketo-hexahydr <SEP> opyrimi <SEP> din.
EMI0001.0002
Subject <SEP> of the present <SEP> additional patent
<tb> <SEP> is a <SEP> process <SEP> for <SEP> production <SEP> of
<tb> 3'- <SEP> methyl.- <SEP> cyclopentane <SEP> -1 ', 5 <SEP> -spiro-1-methyl 2,4,6, = triketa-hexa @ hyd @ ropyrimidine, <SEP > which one. <SEP> because <SEP> is identified by <SEP>., <SEP> that <SEP> man <SEP> 3-methyl cycl'o # pentane-1-cyan-1 - ca, rbon <SEP>, acid resiter <SEP> with
<tb> methyl urine <SEP> condenses <SEP> and <SEP> the <SEP> get teno <SEP> product <SEP> then <SEP> the <SEP> hydrolysis
<tb> subject.
<tb>
The <SEP> new <SEP> product <SEP> forms <SEP> colorless <SEP> needles
<tb> vom <SEP> F. <SEP> 113-114 <SEP> u, nd <SEP> has <SEP> narcotic
<tb> effect.
<tb>
<I> Example: </I>
<tb> To <SEP> a <SEP> solution <SEP> of <SEP> 4.6 <SEP> parts <SEP> sodium metal <SEP> in <SEP> 100 <SEP> volume parts <SEP> absolute < SEP> Me t: hanol <SEP> <SEP> one <SEP> 18.3 <SEP> parts <SEP> 3-methyl-cyclo, pentane-1-cyano-1-carbonic acid ethyl ester <SEP> and
<tb> 8 <SEP> parts <SEP> methyl # urea <SEP> and <SEP> heated <SEP> 10 <SEP> hours <SEP> under <SEP> reflux.
<SEP> After <SEP> the <SEP> distilling off the methanol, the residue is boiled for 8 hours with the seafold amount of sulfuric acid (2.5 <B>%). </B> After cooling, it is separated crude product of unchanged ester and recrystallized from ver dilute methanol. The pure P'roldukt has a melting point of 113-114.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH230367T | 1942-07-29 | ||
| CH235231T | 1942-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235231A true CH235231A (en) | 1944-11-15 |
Family
ID=25727470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235231D CH235231A (en) | 1942-07-29 | 1942-07-29 | Process for the preparation of 3'-methyl-cyclopentane-1 ', 5-spiro-1-methyl-2,4,6-triketo-hexahydropyrimidine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH235231A (en) |
-
1942
- 1942-07-29 CH CH235231D patent/CH235231A/en unknown
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