Hydrogen iodide → 2-benzylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 703836Notes

Reaction equation

HRID 703836 reaction equation
[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][C:14](Cl)=[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.[IH:20]>>[CH2:1]([S:8][C:9]1[S:19][C:12]2=[N:13][C:14]([I:20])=[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

3

Reactant 2

HCID 24841Hydrogen iodideHCID 142544242-benzylthio-7-chloro-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 142544252-benzylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 55%

Procedure

A mixture of 12.2 g of the thus obtained 2-benzylthio-7-chloro-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one and 124 g of 57% hydroiodic acid was heated to 100°-105° C. and stirred for 4 hours. After cooling, the mixture was filtered and the solid was washed with water and dissolved in chloroform. The organic layer was washed with a sodium hydrogen carbonate aqueous solution, a sodium thiosulfate aqueous solution and water, and dried over anhydrous sodium sulfate. The solvent was distilled off and thus 13.9 g of 55% pure 2-benzylthio-7-iodo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 48%.

Workup

  1. temperaturewas heated to 100°-105° C.
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washthe solid was washed with water
  5. dissolutiondissolved in chloroform
  6. washThe organic layer was washed with a sodium hydrogen carbonate aqueous solution
  7. dry with materiala sodium thiosulfate aqueous solution and water, and dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-dcd673492e784ecbb6ec86ee9ac05dfa
Source dataset
uspto-grants-1991_01
Patent number
US04985432

Reaction notes

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