CH192068A - Process for the preparation of a 3- (dioxypropyl-oxyethyl) -amino-4-oxy-3'-amino-4'-oxyarsenobenzene sulfoxylate. - Google Patents
Process for the preparation of a 3- (dioxypropyl-oxyethyl) -amino-4-oxy-3'-amino-4'-oxyarsenobenzene sulfoxylate.Info
- Publication number
- CH192068A CH192068A CH192068DA CH192068A CH 192068 A CH192068 A CH 192068A CH 192068D A CH192068D A CH 192068DA CH 192068 A CH192068 A CH 192068A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- sulfoxylate
- dioxypropyl
- oxyethyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VYGBQXDNOUHIBZ-UHFFFAOYSA-L sodium formaldehyde sulphoxylate Chemical compound [Na+].[Na+].O=C.[O-]S[O-] VYGBQXDNOUHIBZ-UHFFFAOYSA-L 0.000 claims description 2
- 150000001495 arsenic compounds Chemical class 0.000 claims 1
- 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 description 2
- FKHNQSIOGWGQNY-UHFFFAOYSA-L [Na+].[Na+].[O-]S[O-] Chemical compound [Na+].[Na+].[O-]S[O-] FKHNQSIOGWGQNY-UHFFFAOYSA-L 0.000 description 2
- 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 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines 3-(Diogypropyl-ogyäthyl)-amino-4-ogy-3'-amino-4'- ozyarsenobenzolsulfogylats. Das Hauptpatent betrifft ein Verfahren zur Herstellung von 3-(Bis--dioxypropyl) amino-4,4'-@dioxyarsenobenzol-,3'-aminomono- forma1,dehyd@sulfoxylatnatrium, welches da durch gekennzeichnet ist, @dass man Glycid mit einer Lösung von 3;
3' - Diamino - 4,4' dioxyarsenobenzolmonof ormaldehyd-sulf oxy- latnatrium zur Umsetzung bringt.
Es wurde nun gefunden, dass, man zu einer Verbindung von gleich wertvollen phar makologischen -Eigenschaften auch gelangen kann, wenn man eine Lösung von 3,3'-Di- amino - 4,4' - dioxyarsenobenzolmonoformal - dehydsulfoxylatnatrium, Glycid und Ithy- lenoxyd aufeinander einwirken lässt.
Das auf diese Weise erhältliche 3 - (Dioxypropy 1- oxyäthyl) - amino-4,4' - dioxyarsenobenzol- 3'- aminoformaldehyd,sulfoxylatnatrium bildet ein in Wasser leicht lösliches, in Äther und Athylalkohol unlösliches gelbes Pulver: Es soll als Heilmittel Verwendung finden.
<I>Beispiel:</I> 77,5 g 3"3'-Diamino-4,4'-dioxyarsenoben- zolmonoforma1,delhydsulfoxylatnatrium wer den in Wasser gelöst, zunächst 7,4 g Glycid eingerührt, wobei die Temperatur von 19 auf 21 steigt, und nach dem Abkühlen 4,4 g Äthylenoxyd hinzugefügt. Die beiden Alky- lenoxyde können auch in umgekehrter Rei henfolge eingeführt werden.
Aus der klaren gelben Lösung scheidet sich auf Zusatz von Äthylalkohol und Äther ein ,gelber Nieder schlag von 3-(Dioxypropyl-oxyäthyl)-amino 4,4'-dioxyarsen6benzol=3'-aminoformaldehyd- sulfoxylatnatrium
EMI0002.0001
aus,, der abgesaugt und gegebenenfalls zwecks weiterer Reinigung in Wasser .gelöst und wiederum mittels Äthylalkohol und Äther gefällt wird.
Das Sulfoxylat löst sich leicht in Wasser mit schwach alkalischer Reaktion und enthält etwa<B>19%</B> Arsen.
Process for the preparation of a 3- (diogypropyl-ogyäthyl) -amino-4-ogy-3'-amino-4'-ozyarsenobenzolsulfogylats. The main patent relates to a process for the production of 3- (bis - dioxypropyl) amino-4,4 '- @ dioxyarsenobenzene-, 3'-aminomonoforma1, dehyd @ sulfoxylate sodium, which is characterized by @ that one glycide with a Solution of 3;
3 '- Diamino - 4,4' dioxyarsenobenzene monoformaldehyde sulfoxylate sodium brings to implementation.
It has now been found that a compound of equally valuable pharmacological properties can also be obtained if a solution of 3,3'-di-amino-4,4'-dioxyarsenobenzene monoformal - dehydsulfoxylate sodium, glycide and itethylene oxide is used can interact.
The 3 - (dioxypropy 1-oxyethyl) - amino-4,4'-dioxyarsenobenzene- 3'-aminoformaldehyde, sulfoxylate sodium obtainable in this way forms a yellow powder that is easily soluble in water and insoluble in ether and ethyl alcohol: It is said to be used as a medicinal product .
<I> Example: </I> 77.5 g of 3 "3'-diamino-4,4'-dioxyarsenoben- zolmonoforma1, sodium sulfoxylate are dissolved in water, 7.4 g of glycide are first stirred in, the temperature rising from 19 to 21 rises, and after cooling, 4.4 g of ethylene oxide are added. The two alkylene oxides can also be introduced in the reverse order.
On the addition of ethyl alcohol and ether, a yellow precipitate of 3- (dioxypropyl-oxyethyl) -amino 4,4'-dioxyarsen6benzene = 3'-aminoformaldehyde sulfoxylate sodium separates from the clear yellow solution
EMI0002.0001
from ,, which is sucked off and, if necessary, dissolved in water for the purpose of further cleaning and then precipitated again using ethyl alcohol and ether.
The sulfoxylate dissolves easily in water with a weakly alkaline reaction and contains about <B> 19% </B> arsenic.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE192068X | 1934-03-10 | ||
| CH186394T | 1934-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192068A true CH192068A (en) | 1937-07-15 |
Family
ID=25721360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192068D CH192068A (en) | 1934-03-10 | 1934-12-12 | Process for the preparation of a 3- (dioxypropyl-oxyethyl) -amino-4-oxy-3'-amino-4'-oxyarsenobenzene sulfoxylate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192068A (en) |
-
1934
- 1934-12-12 CH CH192068D patent/CH192068A/en unknown
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