DE967074C - Process for the preparation of basic pyrazolone derivatives - Google Patents
Process for the preparation of basic pyrazolone derivativesInfo
- Publication number
- DE967074C DE967074C DET7573A DET0007573A DE967074C DE 967074 C DE967074 C DE 967074C DE T7573 A DET7573 A DE T7573A DE T0007573 A DET0007573 A DE T0007573A DE 967074 C DE967074 C DE 967074C
- Authority
- DE
- Germany
- Prior art keywords
- basic
- phenyl
- preparation
- dimethyl
- pyrazolone derivatives
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Es wurde gefunden, daß sich 2 Mol i-Phenyl-2, 3-dimethyl-pyrazolon-(5) mit 1 Mol Pyridinaldehyd oder dessen Homologen bzw. Substitutionsprodukten in Anwesenheit von wasserabspaltenden Mitteln, z. B. konzentrierten Säuren, vorzugsweise konzentrierte Schwe-It was found that 2 moles of i-phenyl-2, 3-dimethyl-pyrazolon- (5) with 1 mole of pyridine aldehyde or its homologues or substitution products in the presence of dehydrating agents, e.g. B. concentrated acids, preferably concentrated sulfur
C6H5-NCC 6 H 5 -NC
zu verstehen, das aus dem obengenannten i-Phenyl-2, 3-dimethyl-pyrazolon-(5) durch Wegnahme des an das C-Atom der 4-Stellung gebundenen Η-Atoms hervorgeht. Die erhaltenen Kondensationsprodukte haben feisäure, in guter Ausbeute zu Bis-(i-phenyl-2, 3-dimethyl-pyrazolon-(5)-yl-(4))-(pyridyl)-methanen kondensieren lassen. Unter i-Phenyl-2, 3-dimethyl-pyrazolon-(5)-yl ist hier und im folgenden das einwertige Radikalto understand that from the above-mentioned i-phenyl-2, 3-dimethyl-pyrazolone- (5) emerges from the removal of the Η-atom bonded to the carbon atom in the 4-position. The condensation products obtained have fisiac acid, in good yield to bis (i-phenyl-2,3-dimethyl-pyrazolon- (5) -yl- (4)) - (pyridyl) methanes let condense. Among i-phenyl-2, 3-dimethyl-pyrazolon- (5) -yl is here and in the following the monovalent radical
IlIl
SN C S NC
ι ιι ι
CH3 CH3 CH 3 CH 3
teilweise als solche direkte Heilmitteleigenschaften, teilweise bilden sie wichtige Ausgangsstoffe zur Herstellung weiterer Heilmittel. Sie üben gute antipyretische, analgetische und spasmoly tische Wirkungen aus.partly as such direct remedy properties, partly they form important starting materials for production other remedies. They have good antipyretic, analgesic and spasmolytic effects.
709 702/37709 702/37
Das Verfahren sei durch die nachstehend .beschriebenen Ausführungsbeispiele näher erläutert. Hinsichtlich der Bezifferung wird die im Schrifttum allgemein übliche Nomenklatur verwendet.The procedure is as described below Embodiments explained in more detail. With regard to numbering, it becomes general in the literature Usual nomenclature used.
Herstellung von Bis-(i-phenyl-2, 3-dimethylpyrazolon-(5)-yl-(4) )-(pyridyl-(2') )-methanPreparation of bis (i-phenyl-2, 3-dimethylpyrazolon- (5) -yl- (4) ) - (pyridyl- (2 ')) methane
CH3 CH3 CH 3 CH 3
CfiHsCfiHs
-C -C-C -C
0 00 0
C6H5-C 6 H 5 -
-C-C
IlIl
-C-C
(Konstitutionsformel)(Constitutional formula)
CH3 CH 3
40 Gewichtsteile 1-Phenyl-2, 3-dimethyl-pyrazolon-(5) werden in 40 Gewichtsteilen Salzsäure (D i, 19) suspendiert und mit 11 Gewichtsteüen Pyridin-2-aldehyd etwa 1 Stunde auf 90 bis 95 ° erhitzt. Das intensiv rotgefärbte Reaktionsgemisch wird anschließend mit reichlich Wasser verdünnt und mit schwachem Ammoniakwasser bis zur ammoniakalischen Reaktion versetzt. Beim Erkalten fällt die freie Base als gelblich gefärbte kristalline Masse aus. Von dieser wird abgesaugt, der Rückstand mit Wasser gewaschen und bei etwa 80° getrocknet. Die Rohausbeute beträgt ungefähr 85%·40 parts by weight of 1-phenyl-2, 3-dimethyl-pyrazolone- (5) are in 40 parts by weight of hydrochloric acid (D i, 19) suspended and with 11 parts by weight of pyridine-2-aldehyde heated to 90 to 95 ° for about 1 hour. The intensely red colored reaction mixture is then with copiously diluted with water and mixed with weak ammonia water until the ammoniacal reaction occurs. On cooling, the free base precipitates as a yellowish colored crystalline mass. From this is sucked off, the residue is washed with water and dried at about 80 °. The raw yield is about 85%
Zur Reinigung wird das Rohprodukt in Aceton suspendiert, am Rückflußkühler gekocht und bis zur Lösung mit Alkohol versetzt. Beim Erkalten scheidet sich das Bis-(i-phenyl-2, 3-dimethyl-pyrazolon-(5)-yl-(4))-(pyridyl-(2')) -methan in weißen Kristallen ab. Schmp.: 2120 (Kofier). Bruttoformel: C28H27O2N5; Molgewicht = 465,536.For purification, the crude product is suspended in acetone, boiled in a reflux condenser and mixed with alcohol until it dissolves. On cooling, the bis (i-phenyl-2, 3-dimethyl-pyrazolon- (5) -yl- (4)) - (pyridyl- (2 ')) methane separates out in white crystals. M.p .: 212 0 (Kofier). Gross Formula: C 28 H 27 O 2 N 5 ; Molecular Weight = 465.536.
Darstellung von Bis-(i-phenyl-2, 3-dimethylpyrazolon-(5)-yl-(4) )-(pyridyl-(4') )-methanPreparation of bis (i-phenyl-2, 3-dimethylpyrazolon- (5) -yl- (4) ) - (pyridyl- (4 ')) methane
100 Gewichtsteile i-Phenyl-2, 3-dimethyl-pyrazo-100 parts by weight of i-phenyl-2, 3-dimethyl-pyrazo-
lon-(5) werden in 100 Gewichtsteile konzentrierte Schwefelsäure eingetragen und unter Umrühren nach und nach mit 27,5 Gewichtsteüen Pyridin-4-aldehydIon- (5) are added to 100 parts by weight of concentrated sulfuric acid and added while stirring and after with 27.5 parts by weight of pyridine-4-aldehyde
versetzt. Die Reaktion setzt sofort unter erheblicher Wärmeentwicklung ein. Zur Vervollständigung der Umsetzung wird noch Y2 Stunde auf 90 bis 95 ° erwärmt. Das sirupöse Kondensationsprodukt gibt man in eine verdünnte Ammoniaklösung, wobei die Base als fast weißes Kristallpulver ausgeschieden wird. Rohausbeute etwa 80%.offset. The reaction starts immediately with a considerable development of heat. To complete the reaction, Y is heated to 90 to 95 ° for 2 hours. The syrupy condensation product is poured into a dilute ammonia solution, the base separating out as an almost white crystal powder. Raw yield about 80%.
Zur Reinigung löst man die getrocknete Substanz in warmem Chloroform oder Benzol und scheidet sie durch Zusatz von Petroläther ab. Dann nimmt man in heißem Alkohol auf und versetzt mit Wasser bis zum Auftreten einer Trübung. Beim Erkalten und Stehenlassen resultieren gut ausgebüdete Kristalle vom Schmp. 2420 (Kofier). Bruttoformel: C28H27O2N5; Molgewicht = 465,536.For cleaning, the dried substance is dissolved in warm chloroform or benzene and separated off by adding petroleum ether. Then it is taken up in hot alcohol and water is added until it becomes cloudy. On cooling and leaving to stand, well-formed crystals with a melting point of 242 0 (Kofier) result. Gross Formula: C 28 H 27 O 2 N 5 ; Molecular Weight = 465.536.
Erzeugung von Bis-(i-phenyl-2,3-dimethyl-pyrazolon-(5)-yl-(4) )-(6'-methyl-pyridyl-(2') )-methan.Generation of bis (i-phenyl-2,3-dimethyl-pyrazolon- (5) -yl- (4) ) - (6'-methyl-pyridyl- (2 ')) methane.
Die Durchführung der Reaktion erfolgt im wesentlichen analog dem Beispiel II. Verwendet werden:The reaction is carried out essentially analogously to Example II. The following are used:
100 Gewichtsteüe i-Phenyl-2, 3-dimethyl-pyrazo-100 parts by weight of i-phenyl-2, 3-dimethyl-pyrazo-
lon-(5),lon- (5),
30 „ o-Methyl-pyndin^-aldehyd,30 "o-methyl-pyndine ^ -aldehyde,
100 „ konzentrierte Schwefelsäure.100 "concentrated sulfuric acid.
Nach dem Zusammenbringen der Reaktionskomponenten wird er Ansatz 5 Stunden auf 90 bis 95° erhitzt. Beim Eingießen in verdünnte Ammoniaklösung entsteht zunächst eine zähflüssige Masse. Durch Verrühren mit Aceton und Zugabe von Petroläther erstarrt das Kondensationsprodukt nach kurzer Zeit. Schmp.: 204° (Kofier). Bruttoformel: C29H29O2N5; Molgewicht — 479,562.After the reaction components have been brought together, the batch is heated to 90 ° to 95 ° for 5 hours. When pouring into dilute ammonia solution, a viscous mass is initially created. The condensation product solidifies after a short time by stirring with acetone and adding petroleum ether. Mp .: 204 ° (Kofier). Gross Formula: C 29 H 29 O 2 N 5 ; Molecular Weight - 479.562.
Sämtliche nach obigen Beispielen erhaltenen Basen bilden Salze.All the bases obtained according to the above examples form salts.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET7573A DE967074C (en) | 1953-03-15 | 1953-03-15 | Process for the preparation of basic pyrazolone derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET7573A DE967074C (en) | 1953-03-15 | 1953-03-15 | Process for the preparation of basic pyrazolone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE967074C true DE967074C (en) | 1957-10-03 |
Family
ID=7545628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET7573A Expired DE967074C (en) | 1953-03-15 | 1953-03-15 | Process for the preparation of basic pyrazolone derivatives |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE967074C (en) |
-
1953
- 1953-03-15 DE DET7573A patent/DE967074C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
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