DD229406A1 - PROCESS FOR THE PREPARATION OF 2-AMINO-1,3,4-THIADIAZOL-5-CARBONSAFE AMIDES - Google Patents
PROCESS FOR THE PREPARATION OF 2-AMINO-1,3,4-THIADIAZOL-5-CARBONSAFE AMIDES Download PDFInfo
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- DD229406A1 DD229406A1 DD27032284A DD27032284A DD229406A1 DD 229406 A1 DD229406 A1 DD 229406A1 DD 27032284 A DD27032284 A DD 27032284A DD 27032284 A DD27032284 A DD 27032284A DD 229406 A1 DD229406 A1 DD 229406A1
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- thiadiazole
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- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Amino-1,3,4-thiadiazol-5-carbonsaeureamiden, die als biocide Substanzen oder als Bausteine fuer Folgeprodukte z. B. Farbstoffe von Interesse sind. Ziel der Erfindung ist ein einfaches Verfahren zur Herstellung von 2-Amino-1,3,4-thiadiazol-5-carbonsaeureamiden. Das Wesen der Erfindung besteht darin, dass ein 1,1-Dithiooxalsaeureesteramid in Gegenwart eines Loesungsmittels mit Thiosemicarbazid cyclisiert wird.The invention relates to a process for the preparation of 2-amino-1,3,4-thiadiazole-5-carbonsaeureamiden which are used as biocidal substances or as building blocks for secondary products z. B. dyes are of interest. The aim of the invention is a simple process for the preparation of 2-amino-1,3,4-thiadiazole-5-carboxylic acid amides. The essence of the invention is that a 1,1-dithiooxalic acid ester amide is cyclized in the presence of a solvent with thiosemicarbazide.
Description
VEB CHMIEKOMBINAO? BITTERi1EID 2693VEB CHMIEKOMBINAO? BITTERi 1 EID 2693
\ I Verfahren zur Herstellung von 2-Amino-1,3 »4-thiadiazol-5-carbonsäureamiden\ I Procedure for Preparation of 2-amino-1,3 "4-thiadiazol-5-carboxamides
Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Araino-1,3»4—thiadiazol-5-carbonsäureamiden der FormelThe invention relates to a process for preparing 2-araino-1,3,4-thiadiazole-5-carboxylic acid amides of the formula
I,I,
in der E = HH2» 1^* ^2 ^E = -^1^1' Aryl) bedeutet, die als biocide Substanzen oder als Bausteine für Folgeprodukte z.B. Farbstoffe von Interesse sind.in the E = HH 2 » 1 ^ * ^ 2 ^ E = - ^ 1 ^ 1 'aryl), which are as biocidal substances or as building blocks for secondary products such as dyes of interest.
In der Literatur sind bisher nur Angaben über die Herstellung von 2-Amino-1,3>4—thiadiazol-5-carbonsäure bzw. -ester enthalten. Diese wurden in nur mäßigen Ausbeuten durch Umsetzung von Thiosemicarbazid mit Ethoxalylchlorid oder Oxidation des GIyoxylsäureester-thiosemicarbazons erhalten (Advances in Heterocyclic Chemistry 2, (1968) 173).In the literature so far only information on the preparation of 2-amino-1,3> 4-thiadiazole-5-carboxylic acid or esters are included. These were obtained in only moderate yields by reaction of thiosemicarbazide with ethoxalyl chloride or oxidation of the GIyoxylsäureester thiosemicarbazone (Advances in Heterocyclic Chemistry 2, (1968) 173).
-R ΠΓ7 1QQ / . Ο ! c ο μ ο-R ΠΓ7 1QQ /. Ο! c ο μ ο
- 2 - 2693- 2 - 2693
Ziel der Erfindung ist es, ein Verfahren zur Herstellung von 2-&mino-1,3'»4-thiadiazol-5-carbonsäureamiden zu entwickeln, das die genannten Verbindungen einfach und in guten Ausbeuten zugänglich macht.The aim of the invention is to develop a process for the preparation of 2'-1,3'-4-thiadiazole-5-carboxylic acid amides, which makes said compounds easily and in good yields.
Aufgabe der Erfindung war es, 2-Amino-i,3»4— thiadiazol-5-carbonsäureamide der Formel.I aus geeigneten Oxalsäurederivaten und Thiosemicarbazid zu synthetisieren. Erfindungsgemäß wird die Aufgabe dadurch gelöst, daß ein 1,1-Dithiooxalsäureesteramid der FormelThe object of the invention was to synthesize 2-amino-1,3,4-thiadiazole-5-carboxamides of the formula I from suitable oxalic acid derivatives and thiosemicarbazide. According to the invention the object is achieved in that a 1,1-Dithiooxalsäureesteramid the formula
II.II.
in der E die oben genannte Bedeutung hat undin which E has the meaning given above and
ρ R = Alkyl bedeutet, mit Thiosemicarbazid umgesetztρ R = alkyl, reacted with thiosemicarbazide
wird. Die dabei ablaufende Cyclisierungsreaktion liefert in überraschend hoher Ausbeute die Verbindungen der Formel I, in der R die oben genannte Bedeutung hat.becomes. The cyclization reaction occurring in this process yields, in surprisingly high yield, the compounds of the formula I in which R has the abovementioned meaning.
Die Reaktion erfolgt in einem Lösungsmittel, wie beispielsweise in aliphatischen Alkoholen oder in Dimethylformamid. Ketone sind als Lösungsmittel für die Reaktion nicht geeignet.The reaction takes place in a solvent, such as in aliphatic alcohols or in dimethylformamide. Ketones are not suitable as solvents for the reaction.
Ausführungsbeispiel Allgemeine Vorschrift . Embodiment General rule .
0,01 Mol einer Verbindung der Formel II, in der R die oben0.01 mol of a compound of formula II, in which R is the above
ρ genannte Bedeutung hat und R = CEu ist, wird mit 0,01 Mol Thiosemicarbazid in einem Lösungsmittel 5 bis 8 Stunden erhitzt, bis die H0S- und Mercaptanentwicklung beendet ist. Nach dem Abkühlen wird der ausgefallene Feststoff der Formel I,ρ is as defined and R = CEu is heated with 0.01 mol of thiosemicarbazide in a solvent for 5 to 8 hours until the H 0 S and mercaptan development is complete. After cooling, the precipitated solid of the formula I,
f> O ' f> O '
- 3 - 2693- 3 - 2693
in der R die often genannte Bedeutung hat, abgesaugt und umkristallisiert.in which R has the meaning often mentioned, filtered off with suction and recrystallized.
Tabelle: Lösungsmittel, Ausbeuten und Schmelzpunkte von Verbindungen der Formel ITable: Solvents, yields and melting points of compounds of formula I
Claims (2)
in der R die oben genannte Bedeutung hat und-ι
in which R has the abovementioned meaning and
R = Alkyl ist, in.einem Lösungsmittel mit Thiosemi-2
R = alkyl, in.a solvent with thiosemi
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD27032284A DD229406A1 (en) | 1984-12-05 | 1984-12-05 | PROCESS FOR THE PREPARATION OF 2-AMINO-1,3,4-THIADIAZOL-5-CARBONSAFE AMIDES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD27032284A DD229406A1 (en) | 1984-12-05 | 1984-12-05 | PROCESS FOR THE PREPARATION OF 2-AMINO-1,3,4-THIADIAZOL-5-CARBONSAFE AMIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD229406A1 true DD229406A1 (en) | 1985-11-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD27032284A DD229406A1 (en) | 1984-12-05 | 1984-12-05 | PROCESS FOR THE PREPARATION OF 2-AMINO-1,3,4-THIADIAZOL-5-CARBONSAFE AMIDES |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112209878A (en) * | 2020-10-26 | 2021-01-12 | 上海科技大学 | Cannabinoid receptor light-operated ligand and preparation method and application thereof |
-
1984
- 1984-12-05 DD DD27032284A patent/DD229406A1/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112209878A (en) * | 2020-10-26 | 2021-01-12 | 上海科技大学 | Cannabinoid receptor light-operated ligand and preparation method and application thereof |
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