DE824042C - Process for the preparation of acylaminocyanoacetic esters - Google Patents
Process for the preparation of acylaminocyanoacetic estersInfo
- Publication number
- DE824042C DE824042C DEP13498D DEP0013498D DE824042C DE 824042 C DE824042 C DE 824042C DE P13498 D DEP13498 D DE P13498D DE P0013498 D DEP0013498 D DE P0013498D DE 824042 C DE824042 C DE 824042C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- acylaminocyanoacetic
- esters
- ester
- isonitrosocyanoacetate
- 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
- 238000000034 method Methods 0.000 title claims 2
- 150000002148 esters Chemical class 0.000 title 1
- 239000003929 acidic solution Substances 0.000 claims 1
- -1 amino compound Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Acylaminocyanessigestern Es wurde gefunden, daß man die Acylverbindungen des Aminocyanessigesters in sehr guter Ausbeute erhält, wenn man den Isonitrosocyanessigester in saurer Lösung, zweckmäßig in essigsaurer Lösung, mit einem reduzierend wirkenden Mittel, z. B. mit Zinkstaub, behandelt und auf das Umsetzungsgemisch unmittelbar nach Bildung der Aminoverbindung ein Acylierungsmittel, z. B. die äquivalente Menge eines Säurechlorids, einwirken läßt. Die so erhaltenen Acylaminocyanessigester sind gut kristallisierte Verbindungen, die wertvolle Zwischenprodukte für die Herstellung von Arzneimitteln darstellen.Process for the preparation of acylaminocyanoacetic esters It has been found that the acyl compounds of the aminocyanoacetate are obtained in very good yield, if you have the isonitrosocyanoacetic ester in acidic solution, expediently in acetic acid Solution, with a reducing agent, e.g. B. with zinc dust, treated and an acylating agent on the reaction mixture immediately after formation of the amino compound, z. B. the equivalent amount of an acid chloride, can act. The so obtained Acylaminocyanoacetates are well-crystallized compounds that are valuable intermediates for the manufacture of pharmaceuticals.
Das glatte Gelingen dieser Umsetzung ist überraschend, da die Reduktion z. B. des Isonitrosoacetessigester nach Knorr, Liebigs Annalen Bd.236, S. 217, nicht zum Aminoacetessigester, sondern unter Selbstkondensation zum 2, 4-Dimethylpyrroldicarbonsäureester führt.The smooth success of this implementation is surprising, since the reduction z. B. of Isonitrosoacetoessigester according to Knorr, Liebigs Annalen Vol. 236, p. 217, not to the aminoacetoacetic ester, but with self-condensation to the 2,4-dimethylpyrroldicarboxylic acid ester leads.
Beispiel 2o g Isonitrosocyanessigsäuremethylester der Formel werden unter Zusatz von 300 g Eis in 70 ccm Eisessig gelöst. Unter starkem Rühren und Kühlen werden 20 g Zinkstaub auf einmal zugegeben. Nach 3 bis 5 Minuten werden 22 g Phenylessigsäurechlorid auf einmal zugegeben. Nach kurzer Zeit erstarrt die ganze Lösung zu einem dicken Kristallbrei. Dieser wird abgesaugt, mit Wasser gewaschen und getrocknet. Erhalten wurden 25 g Phenacetylaminocyanessigsäuremethylester, Fp. Z43°, der Formel Auf analoge Weise läßt sich der Acetylaminocyanessigester vom Fp. 13o° darstellen.Example 20 g of methyl isonitrosocyanoacetate of the formula are dissolved in 70 ccm of glacial acetic acid with the addition of 300 g of ice. With vigorous stirring and cooling, 20 g of zinc dust are added all at once. After 3 to 5 minutes, 22 g of phenylacetic acid chloride are added all at once. After a short time, the entire solution solidifies into a thick crystal paste. This is filtered off with suction, washed with water and dried. 25 g of methyl phenacetylaminocyanoacetate, melting point 43 °, of the formula were obtained The acetylaminocyanoacetate with a melting point of 130 ° can be prepared in an analogous manner.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP13498D DE824042C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of acylaminocyanoacetic esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP13498D DE824042C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of acylaminocyanoacetic esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE824042C true DE824042C (en) | 1951-12-10 |
Family
ID=7364646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP13498D Expired DE824042C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of acylaminocyanoacetic esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE824042C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2338254A1 (en) * | 1976-01-13 | 1977-08-12 | Lonza Ag | METHOD FOR PREPARING ETHYL AMINOCYANOACETATE |
| WO2007017088A1 (en) * | 2005-07-25 | 2007-02-15 | Novartis Ag | Amidonitrile compounds |
-
1948
- 1948-10-02 DE DEP13498D patent/DE824042C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2338254A1 (en) * | 1976-01-13 | 1977-08-12 | Lonza Ag | METHOD FOR PREPARING ETHYL AMINOCYANOACETATE |
| WO2007017088A1 (en) * | 2005-07-25 | 2007-02-15 | Novartis Ag | Amidonitrile compounds |
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