CH197211A - Process for the preparation of a salt of monoguaiacyl phosphoric acid. - Google Patents
Process for the preparation of a salt of monoguaiacyl phosphoric acid.Info
- Publication number
- CH197211A CH197211A CH197211DA CH197211A CH 197211 A CH197211 A CH 197211A CH 197211D A CH197211D A CH 197211DA CH 197211 A CH197211 A CH 197211A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- salt
- monoguajacylphosphoric
- quinine
- sep
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 title 1
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 9
- 229960000948 quinine Drugs 0.000 claims description 9
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
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)
Description
Verfahren zur HerstelInng eines Salzes der blonognajacylphosphorsänre. Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung eines Äthylendi- aminsalzes der Diguajacylphosphorsäure, wel ches dadurch gekennzeichnet ist, dass auf 2 Mol Diguajacylphoaphorsäure 1 Mol Äthylen diamin zur Einwirkung gebracht wird.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Salzes der Monoguajacylphosphorsäure, welches da durch gekennzeichnet ist, dass man auf 1 Mol Monoguajacylphosphorsäure 1 Mol Chinin ein wirken lässt. Das Reaktionsprodukt stellt eine weisse, in Wasser schwer, in Alkohol leicht lösliche Verbindung dar, die aus wässerigem Alkohol kristallisiert und bei 143-145 o C unter Zersetzung schmilzt.
Die Salzbildung gemäss dem Verfahren der Erfindung kann auch durch doppelte Um setzung eines löslichen Salzes der Monoguaja- cylphosphorsäure mit einem Chininsalz in einem Lösungsmittel erzielt werden. Zur Durchführung der Umsetzung ist es zweck mässig eine Lösung von Chinin bezw. eines Chininsalzes zu einer Lösung von Konoguaja- cylphosphorsäure bezw. eines sauren Salzes derselben zuzugeben.
Zur Ausführung des erfindungsgemässen Verfahrens kann man auch ein Säurederivat der Monoguajacylphosphor- säure, in welchem die an das Phosphoratom ge bundenen Hy droxylgruppen durch austausch bare Reste z. B. Halogen ersetzt sind, bei Anwesenheit von 1 111o1 Chinin oder einem Chininsalz bydrolisieren, wobei intermediär die freie Monoguajacylphosphorsäure entsteht und dann das beschriebene Chininsalz der Monoguajacylphosphorsäure gebildet sein.
Für die Umsetzung werden die beiden Komponenten zweckmässig im oben angege benen molekularen Verhältnis zusammen ge bracht, so dass das Reaktionsprodukt direkt in ausreichender Reinheit erhalten wird oder leicht gereinigt werden kann.
<I>Ausführungsbeispiel:</I> 1/io Mol (26,2 g) Mononatriumsalz der Mono- guajacylphospborsäure werden in 200 cms hei ssem Wasser gelöst und mit einer heissen Lö sung von 39,70 g Chininchlorhydrat ('/io Mol) in 400 crn3 Wasser versetzt. Beim Abkühlen scheidet sich das primäre Chininsalz der Mono- guajacylphosphorsäure nahezu quantitativ ab.
Zur Reinigung kann die so erhaltene Ver bindung aus wässerigem Alkohol umkristalli- siert werden. Die Substanz kristallisiert in nadelförmigen Prismen, ist geruchlos und in kaltem Wasser schwer löslich, in Alkohol dagegen leicht löslich. Sie schmilzt zwischen 143 und 145 C (urikorrigiert) unter Zerset zung.
EMI0002.0008
Für <SEP> C7H905P <SEP> - <SEP> C3oH24N20a <SEP> berechnet <SEP> 38,63 <SEP> % <SEP> C-#H,0rP.
<tb> Durch <SEP> Titration <SEP> gefunden <SEP> 38,61 <SEP> % <SEP> C7Hy05P.
Process for the production of a salt of blonognajacylphosphorsänre. The subject of the main patent is a process for the preparation of an ethylene diamine salt of diguayacylphosphoric acid, wel Ches is characterized in that 1 mol of ethylene diamine is brought into action for every 2 mol of diguayacylphosphoric acid.
The subject of the present patent is a process for the preparation of a salt of monoguajacylphosphoric acid, which is characterized in that 1 mol of quinine is allowed to act on 1 mol of monoguajacylphosphoric acid. The reaction product is a white compound that is difficult to dissolve in water and readily soluble in alcohol, which crystallizes from aqueous alcohol and melts at 143-145 ° C. with decomposition.
The salt formation according to the process of the invention can also be achieved by double reaction of a soluble salt of monoguajacylphosphoric acid with a quinine salt in a solvent. To carry out the implementation, it is appropriate BEZW a solution of quinine. a quinine salt to a solution of Konoguajacylphosphorsäure BEzw. to add an acid salt of the same.
To carry out the process according to the invention, one can also use an acid derivative of monoguajacylphosphoric acid, in which the hydroxyl groups bonded to the phosphorus atom can be exchanged by radicals such. B. halogen are replaced, bydrolize in the presence of 1 111o1 quinine or a quinine salt, whereby the free monoguajacylphosphoric acid is formed as an intermediate and then the quinine salt of monoguajacylphosphoric acid described be formed.
For the reaction, the two components are expediently brought together in the abovementioned molecular ratio so that the reaction product is obtained directly in sufficient purity or can be easily purified.
<I> Exemplary embodiment: </I> 1/10 mol (26.2 g) of the monosodium salt of monoguaacylphosphoric acid are dissolved in 200 cms of hot water and treated with a hot solution of 39.70 g of quinine chlorohydrate (1/10 mol) added to 400 cc of water. On cooling, the primary quinine salt of monoguaacylphosphoric acid separates out almost quantitatively.
For purification, the compound obtained in this way can be recrystallized from aqueous alcohol. The substance crystallizes in needle-shaped prisms, is odorless and poorly soluble in cold water, but easily soluble in alcohol. It melts between 143 and 145 C (uricorrected) with decomposition.
EMI0002.0008
For <SEP> C7H905P <SEP> - <SEP> C3oH24N20a <SEP> <SEP> 38.63 <SEP>% <SEP> C- # H, 0rP is calculated.
<tb> Found by <SEP> titration <SEP> <SEP> 38.61 <SEP>% <SEP> C7Hy05P.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH181648T | 1934-06-23 | ||
| CH197211T | 1937-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH197211A true CH197211A (en) | 1938-04-15 |
Family
ID=25720560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH197211D CH197211A (en) | 1934-06-23 | 1937-04-23 | Process for the preparation of a salt of monoguaiacyl phosphoric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH197211A (en) |
-
1937
- 1937-04-23 CH CH197211D patent/CH197211A/en unknown
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