CH90884A - Process for the preparation of p-arseno-di- (1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone) -monomethylene sulfoxylic acid. - Google Patents
Process for the preparation of p-arseno-di- (1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone) -monomethylene sulfoxylic acid.Info
- Publication number
- CH90884A CH90884A CH90884DA CH90884A CH 90884 A CH90884 A CH 90884A CH 90884D A CH90884D A CH 90884DA CH 90884 A CH90884 A CH 90884A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- dimethyl
- phenyl
- acid
- pyrazolone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 8
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- -1 phenyl- Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 2
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
Description
Verfahren zur Darstellung von p-Arseno-di-(1-phenyl-2 # 3-dimethyl-4-amino-fi-pyrazolon)- monomethylensulfogylsäui e. Es wurde gefunden; dass man p-Arseno-di- (1-phenyl-2 # 3-dirnethyl-4-amino-5-pyrazolorr)- monomethylerisulfoxylsäui-e erhält, wenn man das 1-(Phenyl-p-arsinsäure)-2#3-dimethyl-5-py- razolon nitriert und das entstandene 4-Nitro- 1-(phenyl-p-arsinsäure)
- 2 # 3 -dimethyl- 5-pyra- zolon, dessen Konstitution der Formel
EMI0001.0018
entspricht, mit Formaldehydsulfoxylat be handelt.
Beispiel: .Man trägt.unter Rühren 40 Teile gepul- vertesl -(Plrenyl-p-arsinsäure)-2. 3-dimethyl-5- py razolon in 200 Teile kalte Schwefelsäure ,von 66 0 B6 ein, kühlt diese Lösung auf 0 0 ab und lässt bei 0 bis + 5 0 31 Teile Nitrier- säure (enthaltend .
26 % HN0a) zufliessen. Nach mehrstündigem Rühren giesst man auf 600 Teile Eis, wobei klare Lösung entsteht. Diese wird unter guter Kühlung mit kon zentriertem wässerigem Ammoniak so weit neu tralisiert, d'ass die Flüssigkeit nur noch schwach kongosauer reagiert.
Sodann wird abgekühlt und das kristallinisch ausgeschiedene 1-(Phe- r)yl-p-arsinsäure)-2 # 3-dimethyl-4-nitro-5-pyra- zolon abfiltriert und aus heissem Wasser um kristallisiert. Die Säure ist in kaltem Wasser schwer löslich, leichter in heissem Wasser und kristallisiert daraus in fast weissen Blätt chen oder in derben orangegelben Prismen, die beim Erhitzen verpuffen. In verdünnten Säuren und in Alkalien 'ist die Säure leicht löslich.
3,6 Teile l-Phenyl=p-arsinsäure)-2 # 3-di- methyl-4-nitro-5-pyrazolon werden in 40 Tei len Wasser heiss gelöst und rasch abgekühlt. Zu deni Kristallbrei gibt man unter starkem Rühren<B>16</B> Teile Formaldehydsulfoxylat irr 30 Teilen Wasser gelöst. Nach Zusatz von 10 Teilen Normalsalzsäure wird sodann 5-1O Minuten auf dem Wasserbad erwärmt und weiter. 10 Teile Normalsalzsäure zugefügt.
EMI0002.0001
Man <SEP> .kühlt <SEP> hierauf. <SEP> ab, <SEP> filtriert <SEP> den <SEP> ausge schiedenen <SEP> Niederschlag <SEP> und <SEP> 'wäscht <SEP> ibn,aus.
<tb> Die <SEP> so <SEP> erhaltene <SEP> S_ <SEP> ulfoxylsäure: <SEP> , <SEP> bildet <SEP> ein
<tb> gelbes, <SEP> in <SEP> Alkalien. <SEP> wie <SEP> in <SEP> Säure <SEP> lösliches
<tb> "Pulver.
Process for the preparation of p-arseno-di- (1-phenyl-2 # 3-dimethyl-4-amino-fi-pyrazolone) - monomethylene sulfogyl acid. It was found; that you get p-arseno-di- (1-phenyl-2 # 3-dirnethyl-4-amino-5-pyrazolorr) - monomethylerisulfoxylsäui-e if you get the 1- (phenyl-p-arsinic acid) -2 # 3- dimethyl-5-py- razolon nitrated and the resulting 4-nitro- 1- (phenyl-p-arsinic acid)
- 2 # 3 -dimethyl- 5-pyrazolon, its constitution of the formula
EMI0001.0018
corresponds to be treated with formaldehyde sulfoxylate.
Example: 40 parts of powdered (plrenyl-p-arsinic acid) -2 are carried while stirring. 3-dimethyl-5-pyrazolone in 200 parts of cold sulfuric acid, from 66 0 B6, cools this solution to 0 0 and leaves at 0 to + 5 0 31 parts of nitric acid (containing.
26% HN0a) flow in. After several hours of stirring, the mixture is poured onto 600 parts of ice, a clear solution being formed. This is neutralized under good cooling with concentrated aqueous ammonia to such an extent that the liquid only reacts slightly acidic to the Congo.
It is then cooled and the 1- (Phe- r) yl-p-arsinic acid) -2 # 3-dimethyl-4-nitro-5-pyrazolone which has precipitated out in crystalline form is filtered off and recrystallized from hot water. The acid is sparingly soluble in cold water, more easily in hot water and crystallizes out of it in almost white leaves or in coarse orange-yellow prisms that evaporate when heated. The acid is easily soluble in dilute acids and alkalis.
3.6 parts of 1-phenyl = p-arsinic acid) -2 # 3-dimethyl-4-nitro-5-pyrazolone are dissolved in 40 parts of hot water and quickly cooled. 16 parts of formaldehyde sulfoxylate, dissolved in 30 parts of water, are added to the crystal slurry with vigorous stirring. After adding 10 parts of normal hydrochloric acid, the mixture is then heated on the water bath for 5-10 minutes and then continued. 10 parts of normal hydrochloric acid were added.
EMI0002.0001
<SEP> is then cooled down <SEP>. <SEP> from, <SEP> filters <SEP> the <SEP> separated <SEP> precipitate <SEP> and <SEP> 'washes out <SEP> ibn.
<tb> The <SEP> so <SEP> obtained <SEP> S_ <SEP> ulfoxylic acid: <SEP>, <SEP> forms <SEP>
<tb> yellow, <SEP> in <SEP> alkalis. <SEP> like <SEP> soluble in <SEP> acid <SEP>
<tb> "powder.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE90884X | 1917-12-15 | ||
| CH90186T | 1918-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH90884A true CH90884A (en) | 1921-10-01 |
Family
ID=25704133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH90884D CH90884A (en) | 1917-12-15 | 1918-12-27 | Process for the preparation of p-arseno-di- (1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone) -monomethylene sulfoxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH90884A (en) |
-
1918
- 1918-12-27 CH CH90884D patent/CH90884A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH312530A (en) | Process for making a pyridazone. | |
| AT88635B (en) | Process for the preparation of arsenic compounds of the pyrazolone series. | |
| DE608434C (en) | Process for the preparation of condensation products from 2,3-oxynaphthoic acid and anthranilic acid amide or its substitution products | |
| DE498661C (en) | Process for the preparation of basic derivatives of the nitro-9-aminoacridines | |
| DE587428C (en) | Process for the preparation of 1, 5, 5- and 1, 3, 5, 5-substituted barbituric acids | |
| DE831697C (en) | Process for the preparation of new pyrimidylaminoquinoline derivatives | |
| AT108411B (en) | Process for the preparation of chromates of magnesium. | |
| CH90886A (en) | Process for the preparation of p-arseno-di- (1-phenyl-2. 3-dimethyl-4-amino-5-pyrazolone) -dimethylene sulfoxylic acid. | |
| DE547984C (en) | Process for the preparation of compounds of the alkali salts C, C-disubstituted barbituric acids with pyrazolones | |
| DE715604C (en) | Process for the preparation of 1-phenylsemicarbazide | |
| DE901173C (en) | Process for the preparation of salts of diamidine bases | |
| DE526630C (en) | Process for the preparation of nitro or amino compounds of pyracridone | |
| DE565041C (en) | Process for the preparation of 1-amino-2, 4-dichloroanthraquinone | |
| DE546827C (en) | Process for the preparation of monooxamic acids of 4íñ4'-diaminodiphenyl-1íñ1'-cyclohexane and its substitution products | |
| AT56432B (en) | Process for the preparation of durable, high percentage and poorly soluble zinc sodium hydrosulphite. | |
| DE357752C (en) | Process for the preparation of N-aminoacetyl compounds of 4-amino-1-phenyl-2íñ3-dialkyl-5-pyrazolones | |
| DE330342C (en) | Process for the preparation of primary alkali phosphate | |
| CH235954A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| CH94982A (en) | Process for the preparation of an acridine derivative. | |
| CH416595A (en) | Process for the production of pentafluorophenyl urea or -thiourea | |
| DE2227950A1 (en) | Idazoles, their manufacture and use | |
| CH260741A (en) | Process for the preparation of a des-aza-adenine. | |
| CH122065A (en) | Process for the production of 3,9-dicyanoperylene. | |
| CH200061A (en) | Process for the preparation of a diphenyl series hydrazine. | |
| CH150180A (en) | Process for the preparation of an aminoaryl-cyclohexylamine compound. |