DE80843C - - Google Patents
Info
- Publication number
- DE80843C DE80843C DENDAT80843D DE80843DA DE80843C DE 80843 C DE80843 C DE 80843C DE NDAT80843 D DENDAT80843 D DE NDAT80843D DE 80843D A DE80843D A DE 80843DA DE 80843 C DE80843 C DE 80843C
- Authority
- DE
- Germany
- Prior art keywords
- hydrochloric acid
- hydrazine
- acetylamidophenylhydrazine
- ether
- solution
- 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.)
- Active
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 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 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic Effects 0.000 claims 1
- 235000020127 ayran Nutrition 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 5
- FZERHIULMFGESH-UHFFFAOYSA-N Acetanilide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 229960001413 acetanilide Drugs 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N Ketorolac Chemical class OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- NQRLPDFELNCFHW-UHFFFAOYSA-N Nitroacetanilide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C=C1 NQRLPDFELNCFHW-UHFFFAOYSA-N 0.000 description 1
- 210000002374 Sebum Anatomy 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000000410 anti-febrile Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZAASRHQPRFFWCS-UHFFFAOYSA-P diazanium;oxygen(2-);uranium Chemical compound [NH4+].[NH4+].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[U].[U] ZAASRHQPRFFWCS-UHFFFAOYSA-P 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000486 side effect Toxicity 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
Bekanntlich hat das Antifebrin (Acetanilid) antifebrile Eigenschaften, verursacht aber durch seine leichte Verseifbarkeit im menschlichen Organismus oft unerwünschte Nebenwirkungen.It is well known that antifebrin (acetanilide) has antifebrile properties, but is caused by its easy saponifiability in the human organism often has undesirable side effects.
In der Absicht, zu einer Körperklasse zu kommen, die das Acetanilid an andere therapeutisch wirkende Körper gebunden enthalten, hat Erfinder dasselbe in ein bisher noch unbekanntes Hydrazin übergeführt,' um es in dieser Form mit Aldehyden, Ketonen und Ketonsäuren condensiren zu können. Acetanilid wurde nach bekannter Methode nitrirt, das p-Nitroacetanilid durch Reduction in p-Amidoacetanilid übergeführt (s. Nietzki, B. d. d. ehem. Ges. XVII, 343), das letztere diazotirt und aus der Diazoverbindung nach V. Meyer und Le cc ο (B.. d. d. ehem. Ges. XVI, 2976) mittelst Zinnchlorür in salzsaurer Lösung das salzsaure Acetylamidophenylhydrazin hergestellt.With the intention of coming to a body class that contains the acetanilide bound to other therapeutically active bodies, inventors converted the same into a hitherto unknown hydrazine, 'to convert it into to be able to condense this form with aldehydes, ketones and ketonic acids. Acetanilide was nitrated according to the known method, the p-nitroacetanilide by reduction to p-amidoacetanilide transferred (see Nietzki, B. d. d. former Ges. XVII, 343), the latter diazotized and from the diazo connection according to V. Meyer and Le cc ο (B .. d. d. former Ges. XVI, 2976) The hydrochloric acid acetylamidophenylhydrazine is produced by means of tin chloride in a hydrochloric acid solution.
BeispieirExample
50 g des nach bekannter Methode hergestellten p-Amidoacetanilids werden nach und nach unter Umrühren in ein Gemisch von 100 Cc. Salzsäure (1,19) und 100 g Eis eingetragen. Das salzsaure Salz scheidet sich durch diese Manipulation in fein vertheiltem Zustande aus, ohne dafs eine Abspaltung der Acetylgruppe erfolgt. In diesen durch eine Kältemischung auf mindestens o° abgekühlten Brei werden sehr langsam 100 Cc. einer Natriumnitritlösung, welche im Liter 240 g o.6procentiges Natriumnitrit enthält, eingetragen. Die Temperatur wird immer unter o° gehalten. Das salzsaure Salz löst sich im Verhältnifs des zugegebenen Nitrits, und nachdem das erforderliche Quantum eingetragen, tritt klare Lösung ein. Diese Lösung wird unmittelbar' darauf in eine klare Lösung von 200 g Zinnchlorür in 200 Cc. Salzsäure (1,19) eingegossen; um dabei auftretende Schaumbildung zu verhindern, giebt man einige Cc. Aether zu der Zinnchlorürlösung. Nach dem Mischen klärt sich die Lösung, aus welcher durch Zusatz von cone. Salzsäure nunmehr das salzsaure Salz des p-Acetylamidophenylhydrazins ausgeschieden wird.50 g of the p-amidoacetanilide prepared by a known method are gradually and after stirring into a mixture of 100 Cc. Added hydrochloric acid (1.19) and 100 g of ice. The hydrochloric acid salt separates itself into a finely divided state by this manipulation without splitting off the acetyl group. In these by a cold mixture to at least 0 ° cooled paste very slowly 100 Cc. a sodium nitrite solution, which per liter 240 g or 6 percent Contains sodium nitrite. The temperature is always kept below 0 °. The hydrochloric acid salt dissolves in the proportion of the added nitrite, and after the required Entered Quantum, a clear solution occurs. This solution is immediately followed in a clear solution of 200 g of tin chloride in 200 Cc. Poured hydrochloric acid (1.19); to do it To prevent the formation of foam, give a few Cc. Ether to the tin chloride solution. After mixing, the solution clears, from which the addition of cone. Hydrochloric acid is now the hydrochloric acid salt of p-acetylamidophenylhydrazine is eliminated.
Das salzsaure ρ-Acetylamidophenylhydrazin bildet weifse Krystalle und besitzt alle Eigenschaften eines primären aromatischen Hydrazins. Das Salz wird colirt, durch Absaugen zum gröfsten Theil von der Salzsäure befreit, durch überschüssige Sodalösung zersetzt (etwaige Verunreinigungen werden dadurch abgeschieden), die Lösung erwärmt und heifs filtrirt. Das goldgelbe Filtrat enthält das freie Hydrazin, welches durch Ausschütteln mit einem Gemisch von gleichen Theilen Alkohol und Aether und Verdunsten dieses Gemisches als ein brauner dicker Syrup gewonnen wird. Durch Einstellen in eine Kältemischung erstarrt nach mehrstündigem Stehen die ganze Masse zu einem hellgelben Kuchen, welcher sich zwischen den Fingern zerdrücken läfst und eine Consistenz wie Talg zeigt.The hydrochloric acid ρ-acetylamidophenylhydrazine forms white crystals and has all the properties of a primary aromatic hydrazine. The salt is collected, and most of the hydrochloric acid is removed by suction Excess soda solution decomposes (any impurities are separated out), the solution is warmed and filtered hot. The golden yellow filtrate contains the free hydrazine, which by shaking with a mixture of equal parts alcohol and ether and Evaporation of this mixture is obtained as a brown thick syrup. By setting in a cold mixture, after standing for several hours, the whole mass solidifies into a light yellow cake, which is between the fingers can be crushed and shows a consistency like sebum.
Das feste Acetylamidophenylhydrazin ist inThe solid acetylamidophenylhydrazine is in
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE80843C true DE80843C (en) |
Family
ID=353365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT80843D Active DE80843C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE80843C (en) |
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0
- DE DENDAT80843D patent/DE80843C/de active Active
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