Sodium Cyanide → 7-cyano-2-hexylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one
Reaction equation
[CH2:1]([S:7][C:8]1[S:18][C:11]2=[N:12][C:13](I)=[CH:14][C:15](=[O:16])[N:10]2[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cu](C#N)[C:20]#[N:21].[C-]#N.[Na+]>CN(C)C=O>[C:20]([C:13]1[N:12]=[C:11]2[S:18][C:8]([S:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:9][N:10]2[C:15](=[O:16])[CH:14]=1)#[N:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
In 100 ml of dimethylformamide, 6 g of 2-hexylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved. To this solution, 1.77 g of copper cyanide and 0.97 g of sodium cyanide were added and the solution was stirred at 100° C. for 1 hour. After the reaction mixture was cooled to room temperature, it was extracted with chloroform and water. The organic layer was washed with water and dried over anhydrous sodium sulfate. Florisil® was added to the organic layer and it was shaken. The solvent was distilled off, and 2.3 g of 7-cyano-2-hexylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 51%.
Workup
- temperatureAfter the reaction mixture was cooled to room temperature
- extractionit was extracted with chloroform and water
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- additionFlorisil® was added to the organic layer and it
- stirringwas shaken
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-43b91d8c819f44e98da72a029d64db07
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04971971
Reaction notes
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