CH199317A - Process for the preparation of 3- (dioxypropyl-oxyethyl) -amino-4-oxy-3'-oxy-4'-amino-arsenobenzene-formaldehyde bisulfite sodium. - Google Patents
Process for the preparation of 3- (dioxypropyl-oxyethyl) -amino-4-oxy-3'-oxy-4'-amino-arsenobenzene-formaldehyde bisulfite sodium.Info
- Publication number
- CH199317A CH199317A CH199317DA CH199317A CH 199317 A CH199317 A CH 199317A CH 199317D A CH199317D A CH 199317DA CH 199317 A CH199317 A CH 199317A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- oxy
- oxyethyl
- dioxypropyl
- arsenobenzene
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052708 sodium Inorganic materials 0.000 title claims description 4
- 239000011734 sodium Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 2
- AWYSLGMLVOSVIS-UHFFFAOYSA-N phenyl(phenylarsanylidene)arsane Chemical class C1=CC=CC=C1[As]=[As]C1=CC=CC=C1 AWYSLGMLVOSVIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 101150032584 oxy-4 gene Proteins 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 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
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- XUIVKWAWICCWIQ-UHFFFAOYSA-M sodium;formaldehyde;hydrogen sulfite Chemical compound [Na+].O=C.OS([O-])=O XUIVKWAWICCWIQ-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Inorganic Compounds Of Heavy Metals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 3-(Diozypropyl-ogyäthyl)-amino-4-oay-3'-ogy-4'- amino-arsonobenzol-formaldehydbisulfitnatrium. Durch die schweizerische Patentschrift Nr. 157187 ist bekannt, dass sich Amino- arsenobenzole durch Umsetzung mit Alkylen- oxyden und Formaldehydbisulfitnatrium zu Oxyalkylaminoarsenobenzol - formaldehydbi- sulfitverbindungen kondensieren. lassen.
Es wurde nun gefunden, dass man 3-(Di- oxypropyl- oxyäthyl) -amino-4-oxy-3'- oxy-4'- amino - arsenobenzol - formaldehydbisulfit- natrium in der Weise herstellen kann, dass man 3-(Dioxypropyl-oxyäthyl)
-amino-4-oxy- benzol-l-arsineäure mit 3-O@xy-4-aminobenzol- 1.-arsinsäure zu dem entsprechenden asymme trischen Arsenobenzolderivat kondensiert und letzteres mit Formaldehydbisulfitnatrium umsetzt.
Die neue Verbindung stellt ein gelbes Pulver dar, welches in Wasser leicht löslich und in Methylalkohol, Äthylalkohol, Äther und Aceton unlöslich ist. Sie soll als Arznei- mittel, insbesondere als Antisyphilitikum Verwendung finden.
<I>Beispiel:</I> 35,1 g 3-(Dioxypropyl-oxyäthyl)-amino- 4-oxybenzol-l-arsinsäure, dargestellt nach der deutschen Patentschrift Nr. 618447, Beispiel 3, und 23,3 g 3-Oxy-4-aminobenzol-l-arsin- säure, erhältlich nach der deutschen Patent schrift Nr. 244166, werden in Salzsäure ge löst und mittels unterphosphoriger Säure in Gegenwart von Jodkali zum salzsauren 3- (Dioxypropyl - oxyäthyl)-amino-4-ogy-3'-oxy- 4'-aminoarsenobenzol reduziert.
Das Präparat löst sich leicht in Wasser. 52 g des salz sauren Salzes werden in wässerigem Methyl alkohol :gelöst, dann 8 cmg 39 %ige Natrium bisulfitlösung zugetropft und hierauf 10 cm' 30 o iger Formaldehyd, zugefügt.
Nach kur zem Nachrühren gibt man nochmals 10,4 em3 Natriumbisulfitlösung, sowie eine Lösung von 13,9 g Natriumsulfit in 42 cm' Wasser hinzu und fällt die neutralisierte Lösung in Ethylalkohol. Hierbei scheidet sich 3-(Di- oxypropyl -,oxyäthyl) -amino-4-oxy-3'-oxy-4' - amino - arsenobenzol - formaldehydbisulfit- natrium der Formel
EMI0002.0011
als gelber Niederschlag aus.
der abgesaugt und mit Äther gewaschen wird. Die Verbin dung löst sich leicht in Wasser.
Process for the preparation of 3- (Diozypropyl-ogyäthyl) -amino-4-oay-3'-ogy-4'-amino-arsonobenzene-formaldehyde bisulfite sodium. From Swiss patent specification No. 157187 it is known that amino arsenobenzenes condense by reaction with alkylene oxides and sodium formaldehyde bisulphite to form oxyalkylaminoarsenobenzene - formaldehyde bisulphite compounds. to let.
It has now been found that 3- (di-oxypropyl-oxyethyl) -amino-4-oxy-3'-oxy-4'-amino-arsenobenzene-formaldehyde bisulfite sodium can be prepared in such a way that 3- (dioxypropyl -oxyethyl)
-amino-4-oxy-benzene-l-arsine acid is condensed with 3-O @ xy-4-aminobenzene- 1.-arsinic acid to form the corresponding asymmetric arsenobenzene derivative and the latter is reacted with sodium formaldehyde bisulfite.
The new compound is a yellow powder which is easily soluble in water and insoluble in methyl alcohol, ethyl alcohol, ether and acetone. It should be used as a medicament, in particular as an antisyphilitic agent.
<I> Example: </I> 35.1 g of 3- (dioxypropyl-oxyethyl) -amino-4-oxybenzene-l-arsinic acid, prepared according to German Patent No. 618447, Example 3, and 23.3 g of 3- Oxy-4-aminobenzene-l-arsinic acid, available according to German Patent No. 244166, are dissolved in hydrochloric acid and using hypophosphorous acid in the presence of potassium iodide to form hydrochloric acid 3- (dioxypropyl-oxyethyl) -amino-4-ogy -3'-oxy-4'-aminoarsenobenzene reduced.
The preparation dissolves easily in water. 52 g of the acidic salt are dissolved in aqueous methyl alcohol, then 8 cmg of 39% sodium bisulfite solution are added dropwise and 10 cm of 30% formaldehyde is then added.
After brief stirring, a further 10.4 cubic meters of sodium bisulfite solution and a solution of 13.9 g of sodium sulfite in 42 cm of water are added, and the neutralized solution is precipitated in ethyl alcohol. This separates 3- (dioxypropyl-, oxyethyl) -amino-4-oxy-3'-oxy-4 '- amino - arsenobenzene - formaldehyde bisulfite sodium of the formula
EMI0002.0011
as a yellow precipitate.
which is sucked off and washed with ether. The compound dissolves easily in water.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE199317X | 1936-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199317A true CH199317A (en) | 1938-08-15 |
Family
ID=5757483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199317D CH199317A (en) | 1936-05-22 | 1937-05-14 | Process for the preparation of 3- (dioxypropyl-oxyethyl) -amino-4-oxy-3'-oxy-4'-amino-arsenobenzene-formaldehyde bisulfite sodium. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199317A (en) |
-
1937
- 1937-05-14 CH CH199317D patent/CH199317A/en unknown
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