DE498051C - Process for the preparation of N-monoacylated diaminoarsenobenzenes - Google Patents
Process for the preparation of N-monoacylated diaminoarsenobenzenesInfo
- Publication number
- DE498051C DE498051C DEI35960D DEI0035960D DE498051C DE 498051 C DE498051 C DE 498051C DE I35960 D DEI35960 D DE I35960D DE I0035960 D DEI0035960 D DE I0035960D DE 498051 C DE498051 C DE 498051C
- Authority
- DE
- Germany
- Prior art keywords
- diaminoarsenobenzenes
- monoacylated
- preparation
- acid
- amino
- 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.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical class O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- KYKXDTPUHIPKNG-UHFFFAOYSA-N dichloroarsane Chemical class Cl[AsH]Cl KYKXDTPUHIPKNG-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring 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
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von N-monoacylierten Diaminoarsenobenzolen In der britischen Patentschrift 248 523 ist die Herstellung von N-Monoacylderivatenvon Diaminoarsenobenzolen durch gemeinschaftliche Reduktion z. B. von 3-Amino-a-oxybenzol-i-arsinsäure und 3-Acetylamino-4-oxybenzol-i-arsinsäure bzw. durch Kondensation von Aminoarylarsinen mit Acylaminoarylarsinoxydenöder den entsprechenden Dichlorarsinen beschrieben. Den Reaktionsverlauf -geben folgende Formelbilder wieder: Es wurde nun gefunden, daß N-monoacylierte Diaminoarsenobenzole durch Behandlang von Diaminoarsenobenzolen mit der zur Acylierung einer Aminogruppe erforderlichen Menge eines Acylierungsmittels glatt -erhalten werden können. Dieser Reaktionsverlauf war nicht vorauszusehen. An Stelle der Acylierung nur einer Aminogruppe unter Bildung der Monoacylverbindung konnte ebensogut ein Teil des Diaminoarsenobenzols diacyliert und der übrige Teil der Base überhaupt nicht angegriffen werden.Process for the preparation of N-monoacylated diaminoarsenobenzenes In British patent specification 248 523 the preparation of N-monoacyl derivatives of diaminoarsenobenzenes by joint reduction e.g. B. of 3-amino-α-oxybenzene-i-arsinic acid and 3-acetylamino-4-oxybenzene-i-arsinic acid or the corresponding dichloroarsines by condensation of aminoarylarsines with acylaminoarylarsineoxydenoder described. The following formulas show the course of the reaction: It has now been found that N-monoacylated diaminoarsenobenzenes can be obtained smoothly by treating diaminoarsenobenzenes with the amount of acylating agent required to acylate an amino group. This course of the reaction could not be foreseen. Instead of acylating only one amino group with the formation of the monoacyl compound, part of the diaminoarsenobenzene could just as well be diacylated and the remaining part of the base could not be attacked at all.
Daß die Reaktion den angegebenen Verlauf nimmt, ergibt sich aus folgendem: Die erhaltenen N-Acylverbindungen sind klar löslich in verdünnter Salzsäure, sind also frei von dem Diacylderivat. Wird das Reaktionsprodukt, welches z. B. durch MonoacetyLerung des 3, 3'-Diamino-4, 4'-dioxyarsenobenzols erhalten wird, mittels Wasserstoffsuperoxyds zu den Arsinsäuren oxydiert, so entstehen äquimolekulare Mengen von 3-Amino-4-oxybenzolarsinsäure und deren N-Acetylderivat. Beispiele 1. 45 g 3, 3'-Diamino-4, 4'-dioxyarsenobenzoldihydrochlorid werden in 450 ccm Wasser gelöst und durch Zugabe von 33,2 ccm Natronlauge (40° B6) in das Phenolat übergeführt. Unter lebhaftem Rühren läßt man io,2 g Essigsäureanhydrid zutropfen. Dabei tritt Temperaturerhöhung ein. Sobald die Temperatur wieder zu fallen beginnt, kühlt man auf etwa io° C ab, fügt 7 ccm Eisessig hinzu, saugt von der Ausscheidung ab, wäscht diese mit Wasser aus und trocknet im Vakuum. Das entstandene 3-Amino-3'-acetylamino-4,4'-dioxyarsenobenzol ist ein blaßgelbes, in verdünnter Natronlauge und verdünnter Salzsäure lösliches Pulver.The fact that the reaction takes the course indicated can be seen from the following: The N-acyl compounds obtained are clearly soluble in dilute hydrochloric acid thus free from the diacyl derivative. If the reaction product, which z. B. by MonoacetyLerung of 3, 3'-diamino-4, 4'-dioxyarsenobenzols is obtained by means of When hydrogen peroxide is oxidized to the arsinic acids, equimolecular amounts are produced of 3-amino-4-oxybenzolaric acid and its N-acetyl derivative. Examples 1. 45 g 3, 3'-Diamino-4,4'-dioxyarsenobenzene dihydrochloride are dissolved in 450 ccm of water and converted into the phenolate by adding 33.2 ccm of sodium hydroxide solution (40 ° B6). 10.2 g of acetic anhydride are added dropwise with vigorous stirring. It occurs Temperature increase. As soon as the temperature starts to drop again, you cool down to about 10 ° C, add 7 cc of glacial acetic acid, suck off the excretion, wash this out with water and dried in a vacuum. The 3-amino-3'-acetylamino-4,4'-dioxyarsenobenzene formed is a pale yellow, soluble in dilute sodium hydroxide solution and dilute hydrochloric acid Powder.
2. Aus 45 g 4, 4@-Diamino-3, 3'-dioxyarsenobenzoldihydrochlorid wird, wie in Beispiel i angegeben, die Phenolatlösung hergestellt, zu dieser anteilsweise 15,5 g Benzoylchlorid gegeben und jeweils geschüttelt, bis das Benzoylchlorid verschwunden ist. Nach Zusatz von 7 ccm Eisessig wird die N-Monobenzoylverbindung, wie in Beispiel i angegeben, abgeschieden und getrocknet. Das Produkt .hat ähnliche Eigenschaften wie das Monoacetyldexivat.2. 45 g of 4, 4 @ -diamino-3, 3'-dioxyarsenobenzene dihydrochloride is as indicated in Example i, the phenolate solution prepared, proportionately to this Given 15.5 g of benzoyl chloride and shaking each time until the benzoyl chloride has disappeared is. After adding 7 cc of glacial acetic acid, the N-monobenzoyl compound becomes as in example i specified, deposited and dried. The product has similar properties like the monoacetyl dexivative.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35960D DE498051C (en) | 1928-11-02 | 1928-11-02 | Process for the preparation of N-monoacylated diaminoarsenobenzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35960D DE498051C (en) | 1928-11-02 | 1928-11-02 | Process for the preparation of N-monoacylated diaminoarsenobenzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE498051C true DE498051C (en) | 1930-05-21 |
Family
ID=7189118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI35960D Expired DE498051C (en) | 1928-11-02 | 1928-11-02 | Process for the preparation of N-monoacylated diaminoarsenobenzenes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE498051C (en) |
-
1928
- 1928-11-02 DE DEI35960D patent/DE498051C/en not_active Expired
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