CH199648A - Process for the preparation of 1-phenyl-2,3-dimethyl-4-thioformylamino-5-pyrazolone. - Google Patents
Process for the preparation of 1-phenyl-2,3-dimethyl-4-thioformylamino-5-pyrazolone.Info
- Publication number
- CH199648A CH199648A CH199648DA CH199648A CH 199648 A CH199648 A CH 199648A CH 199648D A CH199648D A CH 199648DA CH 199648 A CH199648 A CH 199648A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- dimethyl
- pyrazolone
- thioformylamino
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- -1 1-phenyl-2,3-dimethyl-4-thioformylamino-5-pyrazolone Chemical compound 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 4
- WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical class NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- JHXPCSYIECUNMQ-UHFFFAOYSA-M potassium methanedithioate Chemical compound [K+].[S-]C=S JHXPCSYIECUNMQ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/50—Acylated on said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 1-Phenyl-2,3-dimethyl-4-thioformylamino-5-pyrazolon. Thioformylamide wurden bisher gewon- nen,durch Einwirkung von Sohwefelwa"ser- stoff auf Isonitrile oder von Phosphorpenta- sulfid auf Amide der Ameisensäure. Diese Verfahren sind umständlich und liefern das
Produkt meist in sichleehter Ausbeute und schwer zu reinigender Form. Auch sind diese Verfahren, besonders das zweite, bei leicht sieh weiter verändernden Substanzen nicht anwendbar.
Es wurde nun gefunden, d@ass man in ein facher und schonender Weisse zu Thioformyl- amiden in meist vorzüglicher Ausbeute ge langen kann, wenn man Dithioameisensäure oder ihre Salze auf Ammoniak oder Amine einwirken lässt.
Die Umsetzung verläuft unter sehr milden Bedingungen und führt auch dann zum Ziel, wenn weitere leicht Gruppen,
in dem umzu- setzenden Amin enthalten sind. Nach dem beanspruchten Verfahren lässt sich zum Bei spiel o-Phenylendiamin in, die Mono-thio- formylverbindung überführen, obgleich .die zweite Aminogruppe nicht nur ebenfalls thioformyliert werden,
sondern auch zur Benzimidazolbildung Veranlassung geben könnte. Auch darin liegt ein grosser Vorteil der neue Methode, dass sie allgemeiner An wendung fähig ist.
Sowohl aliphatische, hydroaromatismhe und aromatisthe Amine verhalten, sich gegenüber Dithioameisensäure und ihren .Salzen: gleich; auch Amine hetero- cyolischer Ringsysteme bilden keine Au,5- nahme.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von 1-Phenyl- 2,3--dimethyl-4-thiofown.ylamino-5-pyrazolon, welches dadurch gekennzeichnet ist, -dass man Dithioameisensäure oder ihre Salze auf 1-Phenyl- 2-,3-idimethyl-4-amino-5-pyrazolon unter Anwendung eines Lösungsmittels ein wirken lässt.
Das l--Phenyl-)2,:3-idimethyl-4-thioformyl- amino-5-pyrazol.on ist neu, es, bildet kleine gelbstichige, in Wasser schwerlösliche Kri- stalle, die bei. M' schmelzen, und stellt ein Zwischenprodukt für die Gewinnung von pharmazeutisch wichtigen Verbindungen dar.
<I>Beispiel:</I> 123 Gewichtsteile 1-Phenyl-2,3-dimethyl- 4-amino-5-pyrazolon wenden in 1000 Ge wichtsteilen Wasser gelöst und mit einer Lösung von 140 Gewichtsteilen. Kalium- dithioformiat in 300 Gewichtsteilen Wasser versetzt.
Das 1-Phenyl-2,3-limethyl-4-thio- formy lamino-5-pyrazolon scheidet sich bereits nach einigen Minuten in kleinen gelbstiehi- gen Kristallen ab. Nach 12, Stunden trennt man die Kristalle von der Flüssigkeit und wäscht sie mit Wasser.
Process for the preparation of 1-phenyl-2,3-dimethyl-4-thioformylamino-5-pyrazolone. Up to now, thioformylamides have been obtained by the action of sulphurous hydrogen on isonitriles or of phosphorus pentasulphide on amides of formic acid. These processes are laborious and provide that
Product mostly in low yield and difficult to clean form. These methods, especially the second, are also not applicable to substances that change slightly.
It has now been found that thioformylamides can be obtained in a simple and gentle manner in mostly excellent yields if dithioformic acid or its salts are allowed to act on ammonia or amines.
The implementation takes place under very mild conditions and leads to the goal even if other easy groups,
are contained in the amine to be reacted. According to the claimed process, for example, o-phenylenediamine can be converted into the mono-thio-formyl compound, although the second amino group is not only thioformylated as well,
but could also give rise to benzimidazole formation. Another major advantage of the new method is that it can be used in general.
Both aliphatic, hydroaromatic and aromatic amines behave in the same way with respect to dithioformic acid and its salts: the same; amines of heterocyclic ring systems also do not form an acceptance.
The subject of the present patent is a process for the preparation of 1-phenyl-2,3-dimethyl-4-thiofown.ylamino-5-pyrazolone, which is characterized in that dithioformic acid or its salts are based on 1-phenyl 2- , 3-idimethyl-4-amino-5-pyrazolone can act using a solvent.
The l-phenyl-) 2,: 3-idimethyl-4-thioformylamino-5-pyrazol.one is new, it forms small yellowish crystals that are sparingly soluble in water, which at. M 'melt, and is an intermediate product for the production of pharmaceutically important compounds.
<I> Example: </I> 123 parts by weight of 1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone are dissolved in 1000 parts by weight of water and mixed with a solution of 140 parts by weight. Potassium dithioformate is added to 300 parts by weight of water.
The 1-phenyl-2,3-limethyl-4-thioformylamino-5-pyrazolone separates out in small, yellowish crystals after just a few minutes. After 12 hours, the crystals are separated from the liquid and washed with water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH192572T | 1936-08-14 | ||
| CH199648T | 1936-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199648A true CH199648A (en) | 1938-08-31 |
Family
ID=25722292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199648D CH199648A (en) | 1936-08-14 | 1936-08-14 | Process for the preparation of 1-phenyl-2,3-dimethyl-4-thioformylamino-5-pyrazolone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199648A (en) |
-
1936
- 1936-08-14 CH CH199648D patent/CH199648A/en unknown
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