DE248956C - - Google Patents
Info
- Publication number
- DE248956C DE248956C DENDAT248956D DE248956DA DE248956C DE 248956 C DE248956 C DE 248956C DE NDAT248956 D DENDAT248956 D DE NDAT248956D DE 248956D A DE248956D A DE 248956DA DE 248956 C DE248956 C DE 248956C
- Authority
- DE
- Germany
- Prior art keywords
- chloroform
- alcohol
- boiled
- ammonia
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical class OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003016 phosphoric acids Chemical class 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- -1 ester amides Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 159000000009 barium salts Chemical class 0.000 description 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical group 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 248956 KLASSE 12 o. GRUPPE- M 248956 CLASS 12 or GROUP
Dr. KURT LANGHELD in BRESLAU.Dr. KURT LANGHELD in BRESLAU.
Patentiert im Deutschen Reiche vom 22. Juni 1910 ab.Patented in the German Empire on June 22, 1910.
Das vorliegende Verfahren betrifft die Herstellung von Abkömmlingen der Phosphorsäure aus Körpern, welche eine alkoholische Hydroxylgruppe enthalten, oder organische Abkömmlinge des Ammoniaks sind. Die Verbindungen sind für therapeutische Zwecke verwendbar. The present process relates to the preparation of derivatives of phosphoric acid from bodies containing an alcoholic hydroxyl group or organic derivatives of ammonia. The compounds are useful for therapeutic purposes.
Wenn man Alkylester, z. B. den Äthylester der Metaphosphorsäure auf Alkohol, Ammoniak oder Ammoniakderivate einwirken läßt, so entstehen Monoester, Diester oder Esteramide der Orthophosphorsäure.When using alkyl esters, e.g. B. the ethyl ester of metaphosphoric acid on alcohol, ammonia or ammonia derivatives act, monoesters, diesters or ester amides are formed of orthophosphoric acid.
50 kg Metaphosphorsäureäthylester, gewonnen durch Kochen von Diäthyläther mit Phosphor pen toxyd, werden mit 50 kg absolutem Alkohol 3 Stunden gekocht. Das Reaktionsprodukt wird in folgender Weise verarbeitet:50 kg of ethyl metaphosphorate obtained by boiling diethyl ether with phosphorus pen toxyd, 50 kg of absolute Alcohol boiled for 3 hours. The reaction product is processed in the following way:
Es wird zunächst der Alkohol abgedunstet und dann durch Destillation der Triäthylphosphorsäureester von dem Diäthylphosphorsäureester getrennt. Die Ausbeute ist quantitativ.First the alcohol is evaporated and then the triethylphosphoric acid ester by distillation separated from the diethylphosphoric acid ester. The yield is quantitative.
50 g feinst gepulverte Glykose werden in einer Lösung von 80 g Metaphosphorsäureäthylester in 1000 ecm Chloroform aufgeschlemmt und 20 Stunden gekocht. Der Zucker färbt sich während der Behandlung schwach gelb und ballt sich zusammen. Er wird von Chloroform getrennt und mit 1000 ecm50 g of finely powdered glycose are dissolved in a solution of 80 g of ethyl metaphosphate Suspended in 1000 ecm of chloroform and boiled for 20 hours. Of the Sugar turns pale yellow and agglomerates during treatment. He is separated from chloroform and with 1000 ecm
(CHJ2- CH- CH2- CH(CHJ 2 - CH - CH 2 - CH
Beim Verdunsten des Chloroforms hinterbleibt ein dicker Sirup, der außer in Chloroform in absolutem Alkohol löslich ist. Die Substanz absolutem Alkohol ausgekocht. Der verbleibende Rückstand enthält noch Traubenzucker. Der neu entstandene Körper wird durch wiederholtes Waschen mit Wasser von der Glykose getrennt. Es liegt ein Phosphorsäureester der Glykose vor. Die Substanz reduziert außerdem Fehlingsche Lösung beim Erwärmen und bildet ein Osazon. Sie ist in Ammoniak, Natronlauge und Barytwasser löslich.· Ein undeutlich kristallinisches Bariumsalz konnte durch Fällen seiner wäßrigen Lösung mit Alkohol erhalten werden. Aus dem alkoholischen Extrakt des ursprünglichen Reäktionsproduktes konnte ferner durch fraktioniertes Fällen mit Äther ein zweiter mikrokristallinischer phosphorhaltiger Körper von ähnlichen Eigenschaften wie der erstbeschriebene gewonnen werden, von dem er sich nur durch seine leichte Löslichkeit in Wasser unterscheidet. Er reduziert gleichfalls Fehlingsche Lösung beim Erwärmen und gibt ein Osazon. Er wurde durch Kochen seiner wäßrigen Lösung mit Bariumkarbonat in das Bariumsalz übergeführt und dieses durch Fällen mit Alkohol isoliert.When the chloroform evaporates, a thick syrup is left behind which, in addition to chloroform, is in is soluble in absolute alcohol. The substance boiled down to absolute alcohol. The remaining one The residue still contains grape sugar. The newly created body is repeated through repetition Wash with water separated from the glucose. It is a phosphoric acid ester Glucose before. The substance also reduces Fehling's solution when heated and forms an osazon. It is soluble in ammonia, caustic soda and barite water. · A indistinct crystalline barium salt could be obtained by precipitating its aqueous solution with alcohol can be obtained. From the alcoholic extract of the original reaction product Furthermore, through fractional precipitation with ether, a second microcrystalline one could be created Phosphorus-containing body with properties similar to those first described from which it differs only in its easy solubility in water. He also reduces Fehling's solution when heated and gives an osazon. He was converted into the barium salt by boiling its aqueous solution with barium carbonate and this isolated by precipitation with alcohol.
Beispiel III. 6s Example III. 6s
Man kocht eine Aufschlämmung von 10 g Leucin mit einer Auflösung von 20 g Metaphosphorsäureäthylester in 500 ecm Chloroform kurze Zeit. Das entstehende Produkt hat folgende Zusammensetzung:A slurry of 10 g of leucine with a dissolution of 20 g of ethyl metaphosphate is boiled in 500 ecm chloroform for a short time. The resulting product has the following Composition:
PO (OH) (OC2H5) (OH)(OC2H5)PO (OH) (OC 2 H 5 ) (OH) (OC 2 H 5 )
6060
/N/ N
CO2H.CO 2 H.
wird durch schwaches Ammoniak leicht unter nahezu quantitativer Rückbildung des Leucins verseift.becomes slightly with almost quantitative regression of the leucine by weak ammonia saponified.
7575
Man kocht eine Aufschlämmung von ioo g Harnstoff mit einer Auflösung von 400 g Metaphosphorsäureäthylester in 1000 ecm Chloroform. Es bildet sich innerhalb einer Stunde in quantitativer Ausbeute das entsprechende Phosphorsäureesteramid des Harnstoffes, das sich vom Chloroform, in dem es unlöslich ist, leicht trennen läßt. Es ist ein dicker, wasserklarer Sirup.A slurry of 100 g of urea with a dissolution of 400 g of ethyl metaphosphate is boiled in 1000 ecm chloroform. It forms within an hour in quantitative yield the corresponding phosphoric acid ester amide of urea, the can easily be separated from chloroform, in which it is insoluble. It's a thick, water-clear one Syrup.
50 g Benzylalkohol in Chloroformlösung mit 100 g Metaphosphorsäureester gekocht liefert in quantitativer Ausbeute den Körper "50 g of benzyl alcohol boiled in chloroform solution with 100 g of metaphosphoric acid ester provides the body in quantitative yield "
β C2 H5 β C 2 H 5
O = P (-OH O = P (-OH
Der Körper ist ein dickes Öl, das in Wasser löslich ist. Man kann ihn über das in Wasser leicht lösliche Bariumsalz reinigen.The body is a thick oil that is soluble in water. You can get it over that in water clean easily soluble barium salts.
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DE248956C true DE248956C (en) |
Family
ID=507621
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