CH224792A - Process for the preparation of 2-methyl-1,4-naphthoquinone-4-sulphurous sodium. - Google Patents
Process for the preparation of 2-methyl-1,4-naphthoquinone-4-sulphurous sodium.Info
- Publication number
- CH224792A CH224792A CH224792DA CH224792A CH 224792 A CH224792 A CH 224792A CH 224792D A CH224792D A CH 224792DA CH 224792 A CH224792 A CH 224792A
- Authority
- CH
- Switzerland
- Prior art keywords
- naphthoquinone
- methyl
- sodium
- preparation
- sulphurous
- Prior art date
Links
- 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 title description 4
- 229910052708 sodium Inorganic materials 0.000 title description 4
- 239000011734 sodium Substances 0.000 title description 4
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- -1 bisulfite compound Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K31/355—Tocopherols, e.g. vitamin E
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung von 2-methyl-1.4-naphthochinon
4-schwefligsaurem Natrium.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 2-methyl1. 4 - naphthochinon - 4 - schwefligsaurem Natnum, welches dadurch gekennzeichnet ist, daB man 2-Methyl-1. 4-naphthochinon mit saurem, schwefligsaurem Natrium umsetzt.
Beispiel :
17, 2 Gewiehtsteile 2-Methyl-1. 4-naphthochinon, 50 Volumteile Wasser, 10 Volumteile Methanol und 60 Volumteile Natriumbisulfitlösung von 39 werden zusammen auf den Dampfbad erhitzt, bis sich alles Chinon mit gelber Farbe gelost hat. Die Losung wird dann im Vakuum eingedampft und der erhaltene Rückstand mit Alkohol behandelt, wobei die Bisulfitverbindung sich l¯st, wÏhrend unverändertes Natriumbisulfit ungelöst bleibt und abgetrennt wird. Die alkoholische Lösung wird eingedampft, der Destillations- rückstand mit wenig Methanol aufgenommen und mit troekenem Äther gefällt.
Dabei er- hÏlt man eine gelbe,zäheSchmiere,die sich beim Trocknen im Vakuum zu einer festen Substanz aufbläht. Beim Verreiben geht sie in ein lockeres, gelbliches, hygroskopisches Pulver über, das gute Vitamin-K-Eigenschaf ten besitzt und in der Therapie verwendet werden soll. Die Ausbeute ist fast quanti tativ.
Das neue Produkt ist in wässriger Lösung, auch bei Gegenwart von SÏure, beständig ; durch Laugen wird es zersetzt.
Es hat die Formel :
EMI1.1
Process for the preparation of 2-methyl-1,4-naphthoquinone
4-sulphurous sodium.
The subject of the present patent is a process for the production of 2-methyl1. 4 - naphthoquinone - 4 - sulphurous sodium, which is characterized by the fact that 2-methyl-1. 4-naphthoquinone reacts with acidic, sulphurous sodium.
Example:
17, 2 parts by weight of 2-methyl-1. 4-naphthoquinone, 50 parts by volume of water, 10 parts by volume of methanol and 60 parts by volume of sodium bisulfite solution of 39 are heated together on the steam bath until all the quinone with a yellow color has dissolved. The solution is then evaporated in vacuo and the residue obtained is treated with alcohol, the bisulfite compound dissolving, while unchanged sodium bisulfite remains undissolved and is separated off. The alcoholic solution is evaporated, the distillation residue is taken up with a little methanol and precipitated with dry ether.
The result is a yellow, viscous smear that expands into a solid substance when it is dried in a vacuum. When rubbed in, it turns into a loose, yellowish, hygroscopic powder that has good vitamin K properties and should be used in therapy. The yield is almost quantitative.
The new product is stable in aqueous solution, even in the presence of acid; it is decomposed by alkalis.
It has the formula:
EMI1.1
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE301139X | 1939-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224792A true CH224792A (en) | 1942-12-15 |
Family
ID=6098206
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224793D CH224793A (en) | 1939-11-30 | 1940-10-16 | Process for the preparation of the sodium salt of 2-methyl-1,4-naphthoquinone-4-succinylhydrazone. |
| CH224792D CH224792A (en) | 1939-11-30 | 1940-10-16 | Process for the preparation of 2-methyl-1,4-naphthoquinone-4-sulphurous sodium. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224793D CH224793A (en) | 1939-11-30 | 1940-10-16 | Process for the preparation of the sodium salt of 2-methyl-1,4-naphthoquinone-4-succinylhydrazone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH224793A (en) |
-
1940
- 1940-10-16 CH CH224793D patent/CH224793A/en unknown
- 1940-10-16 CH CH224792D patent/CH224792A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH224793A (en) | 1942-12-15 |
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