AT32569B - Process for the preparation of methylenzitric acid dihalides. - Google Patents
Process for the preparation of methylenzitric acid dihalides.Info
- Publication number
- AT32569B AT32569B AT32569DA AT32569B AT 32569 B AT32569 B AT 32569B AT 32569D A AT32569D A AT 32569DA AT 32569 B AT32569 B AT 32569B
- Authority
- AT
- Austria
- Prior art keywords
- methylenzitric
- preparation
- acid dihalides
- acid
- parts
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 150000003839 salts Chemical class 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- HGXYMHQZIAWNKI-UHFFFAOYSA-L disodium;2-[4-(carboxylatomethyl)-5-oxo-1,3-dioxolan-4-yl]acetate Chemical compound [Na+].[Na+].[O-]C(=O)CC1(CC([O-])=O)OCOC1=O HGXYMHQZIAWNKI-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- YNOXCRMFGMSKIJ-UHFFFAOYSA-N 2-methylcitric acid Chemical compound OC(=O)C(C)C(O)(C(O)=O)CC(O)=O YNOXCRMFGMSKIJ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Verfahren zur Darstellung von Methylenzitronensäuredihalogeniden.
Bekanntlich ist die Methylenzitronensäure ein relativ leicht zersetzlicher Körper und beruht ja auch ihre therapeutische Wirkung auf der leichten Abspaltbarkeit des Formaldehyds im Organismus. Es musste daher zweifelhaft erscheinen, ob es möglich sein würde, das Diehlorid
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sind wertvolle Zwischenprodukte für die Darstellung von Arzneimitteln.
Beispiel I : 204 Teile Methylenzitronensäure werden mit 420 Teilen Phosphorpentachlorid
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Beendigung der Reaktion destilliert man entweder das entstandene Phosphoroxychlorid ah und kristallisiert den Rückstand aus Benzol und Ligroin um, oder man giesst das füssige Reaktions-
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dann, wie in Beispiel 1 beschrieben, weiter verarbeitet. Das Chlorid kann auch in der Weise isoliert werden, dass man nach dem Abdestillieren des Phosphoroxychlorids unter vermindertem Druck den Rückstand in Petroläther giesst, wobei das Chlorid mit den oben angegebenen Eigenschaften ausfällt.
Beispiel 3 : 204 Teile Methylenzitronensäure werden mit 862 Teilen Phosphorpentabromid auf dem Wasserbade erwärmt, bis alles gelöst ist, Man destilliert darauf das Phosphoroxy-
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Wasser zersetzt es sich sehr leicht in die freie Säure und Bromwasserstoff.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of methylenzitric acid dihalides.
As is well known, methyl citric acid is a relatively easily decomposable body and its therapeutic effect is based on the ease with which formaldehyde can be split off in the body. It must therefore appear doubtful whether it would be possible to use the Diehlorid
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are valuable intermediate products for the preparation of pharmaceuticals.
Example I: 204 parts of methylene citric acid are mixed with 420 parts of phosphorus pentachloride
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When the reaction is complete, either the phosphorus oxychloride formed is distilled and the residue is recrystallized from benzene and ligroin, or the liquid reaction mixture is poured
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then, as described in Example 1, processed further. The chloride can also be isolated in such a way that, after the phosphorus oxychloride has been distilled off, the residue is poured into petroleum ether under reduced pressure, the chloride precipitating with the properties given above.
Example 3: 204 parts of methylene citric acid are heated with 862 parts of phosphorus pentabromide on the water bath until everything has dissolved. The phosphorus oxy-
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In water, it decomposes very easily into the free acid and hydrogen bromide.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1906186659D DE186659C (en) | 1906-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT32569B true AT32569B (en) | 1908-04-10 |
Family
ID=5720039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT32569D AT32569B (en) | 1906-03-22 | 1907-06-03 | Process for the preparation of methylenzitric acid dihalides. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT32569B (en) |
-
1907
- 1907-06-03 AT AT32569D patent/AT32569B/en active
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