DE294731C - - Google Patents
Info
- Publication number
- DE294731C DE294731C DENDAT294731D DE294731DA DE294731C DE 294731 C DE294731 C DE 294731C DE NDAT294731 D DENDAT294731 D DE NDAT294731D DE 294731D A DE294731D A DE 294731DA DE 294731 C DE294731 C DE 294731C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- parts
- nitrosomethylaniline
- hours
- nitro compound
- 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
- 239000002253 acid Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229940093920 gynecological arsenic compound Drugs 0.000 claims description 4
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 150000002828 nitro derivatives Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- -1 aromatic arsenic compounds Chemical class 0.000 claims description 2
- 150000001495 arsenic compounds Chemical class 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 210000001367 artery Anatomy 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 230000009935 nitrosation Effects 0.000 claims 1
- 238000007034 nitrosation reaction Methods 0.000 claims 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AWRGRDOODISXNB-UHFFFAOYSA-N n-[4-(aminomethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(CN)C=C1 AWRGRDOODISXNB-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005245 sintering 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)
- Inorganic Compounds Of Heavy Metals (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE Mq. GRUPPECLASS Mq. GROUP
Zusatz zum Patent 285572 *).Addition to patent 285572 *).
Patentiert im Deutschen Reiche vom 15. Oktober 1912 ab. Längste Dauer: 13. Mai 1927. Patented in the German Empire on October 15, 1912. Longest duration: May 13, 1927.
Das Patent 285572 und dessen Zusätze 286667 und 293842 schützen Verfahren zur Darstellung eines Bismethylaminotetraminoarsenobenzols, welches darin besteht, daß man auf 5 organische Arsenverbindungen des Dimethylanilins Nitriersäure zur Einwirkung bringt und die so erhaltene Dinitromethylnitraminophenyl-p-arsinsäure mit starken Reduktionsmitteln reduziert.Patent 285572 and its additions 286667 and 293842 protect methods of representation a bismethylaminotetraminoarsenobenzene, which consists in that one on 5 brings organic arsenic compounds of dimethylaniline nitrating acid to action and the thus obtained dinitromethylnitraminophenyl-p-arsinic acid with strong reducing agents reduced.
Zu derselben Verbindung gelangt man, wie weiterhin gefunden wurde, wenn man von solchen aromatischen Arsenverbindungen ausgeht, welche in p-Stellung zum Arsenrest dieOne arrives at the same connection, as was further found by going from those aromatic arsenic compounds which are in the p-position to the arsenic residue
Gruppe —Group -
p TTp DD
3 enthalten, worin R = Wasserstoff oder einen Säurerest bedeutet. Unterwirft man solche Verbindungen der Nitrierung, so treten zwei Nitrogruppen in den Benzolkern, die dritte tritt an das Stickstoffatom und ersetzt dort das Wasserstoffatom bzw. den Acidylrest. Es entsteht somit in allen diesen Fällen dieselbe Nitroverbindung" wie nach dem Verfahren des Hauptpatents und des Zusatzpatents 293842, nämlich die Dinitromethylnitraminophenyl-p-arsinsäure, die dann nach den im Hauptpatent bzw. im Zusatzpatent 286667 beschriebenen Methoden zum Bismethyltetraminoarsenobenzol reduziert wird. 3 contain, where R = hydrogen or an acid radical. If such compounds are subjected to nitration, two nitro groups enter the benzene nucleus, the third occurs on the nitrogen atom and there replaces the hydrogen atom or the acidyl radical. In all these cases the same nitro compound is produced as in the process of the main patent and the additional patent 293842, namely dinitromethylnitraminophenyl-p-arsinic acid, which is then reduced to bismethyltetraminoarsenobenzene by the methods described in the main patent or in the additional patent 286667.
Beispiele.
I. Nitrierung von Methylarsanilsäure.Examples.
I. Nitration of methylarsanilic acid.
3030th
4,6 Teile Methylarsanilsäure (erhalten nach dem Verfahren der Patentschrift 250264, Kl. 12°, aus diazotierten! p-Aminomethylacetanilid und nachfolgender Verseifung; weiße kristallinische Verbindung, löslich in heißem Wasser und Alkohol sowie in überschüssiger Salzsäure) trägt man allmählich unter gutem Rühren in 28 Teile rauchender Salpetersäure ein. Wenn alles eingetragen ist, erwärmt man noch 2 Stunden auf dem Wasserbad und gießt nach dem Erkalten auf etwa 80 Teile Eis. Die abgeschiedene Nitroverbindung wird abgesaugt und nach den im Hauptpatent 285572 und dem Zusatzpatent 286667 beschriebenen Methoden zum Bismethyltetraminoarsenobenzol reduziert.4.6 parts of methylarsanilic acid (obtained by the process of patent specification 250264, Kl. 12 °, from diazotized! p-aminomethylacetanilide and subsequent saponification; white crystalline compound, soluble in hot Water and alcohol as well as in excess hydrochloric acid) are gradually carried under good Stir into 28 parts of fuming nitric acid. When everything is entered, one warms up another 2 hours on the water bath and after cooling, pour onto about 80 parts of ice. The precipitated nitro compound is suctioned off and according to the in the main patent 285572 and the additional patent 286667 described methods for bismethyltetraminoarsenobenzene reduced.
II. Nitrierung von Acetylmethylarsanilsäure.II. Nitration of acetylmethylarsanilic acid.
■5,4 Teile Acetylmethylarsanilsäure (erhalten nach der im Beispiel 1 angegebenen Methode; weißes kristallinisches Pulver, löslich in heißem Alkohol und Wasser, schmilzt bei etwa 195 ° unter Sintern zu einer dunkelvioletten Flüssigkeit, mit verdünnten Alkalien zur Methylarsanilsäure verseifbar) werden bei ο bis io° in 30 Teilen Schwefelsäuremono-■ 5.4 parts of acetylmethylarsanilic acid (obtained by the method given in Example 1; white crystalline powder, soluble in hot alcohol and water, melts on about 195 ° with sintering to a dark purple liquid, with dilute alkalis saponifiable to methylarsanilic acid) at ο to io ° in 30 parts of sulfuric acid mono-
*) Frühere Zusatzpatente: 286667, 286668 und 293842.*) Previous additional patents: 286667, 286668 and 293842.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE286667T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE294731C true DE294731C (en) | 1916-10-17 |
Family
ID=6059109
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT286667D Expired DE286667C (en) | |||
| DENDAT285572D Expired DE285572C (en) | |||
| DENDAT286668D Expired DE286668C (en) | |||
| DENDAT293842D Expired DE293842C (en) | |||
| DENDAT294731D Expired DE294731C (en) |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT286667D Expired DE286667C (en) | |||
| DENDAT285572D Expired DE285572C (en) | |||
| DENDAT286668D Expired DE286668C (en) | |||
| DENDAT293842D Expired DE293842C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (5) | DE294731C (en) |
-
0
- DE DENDAT286667D patent/DE286667C/de not_active Expired
- DE DENDAT285572D patent/DE285572C/de not_active Expired
- DE DENDAT286668D patent/DE286668C/de not_active Expired
- DE DENDAT293842D patent/DE293842C/de not_active Expired
- DE DENDAT294731D patent/DE294731C/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE286668C (en) | 1915-08-25 |
| DE286667C (en) | 1915-08-24 |
| DE293842C (en) | 1916-08-25 |
| DE285572C (en) | 1900-01-01 |
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