Sodium Cyanide → 2-benzylthio-7-cyano-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 703838Notes

Reaction equation

HRID 703838 reaction equation
[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][C:14](I)=[CH:15][C:16](=[O:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:20]#[N:21].[Na+]>CN(C)C=O.O>[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][C:14]([C:20]#[N:21])=[CH:15][C:16](=[O:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 142544252-benzylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 142544282-benzylthio-7-cyano-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 120 ml of dimethylformamide, 9 g of 90% pure 2-benzylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was dissolved, and 3.05 g of cuprous cyanide and 1.57 g of sodium cyanide were added thereto. The reaction mixture was heated to 100° C. and stirred at that temperature for 1 hour. After the reaction was finished, the reaction mixture was cooled, diluted with water and extracted with chloroform. The organic layer was washed with water, and the chloroform was distilled off. Water was added to the residue and the mixture was extracted with toluene. The organic layer was washed with water and dried over anhydrous sodium sulfate. Florisil® was added to the dried organic layer, and the organic layer was shaken well. After the Florisil® was separated, the solvent was distilled off, and thus 3.0 g of 2-benzylthio-7-cyano-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 50%. (Florisil® (a registered trademark of Floridin Company) is a highly selective magnesium silicate absorbent.)

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. distillationthe chloroform was distilled off
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with toluene
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. additionFlorisil® was added to the dried organic layer
  10. stirringthe organic layer was shaken well
  11. customAfter the Florisil® was separated
  12. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-14295069bb894932b87dbfdd84390409
Source dataset
uspto-grants-1991_01
Patent number
US04985432

Reaction notes

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