Potassium Iodide → HCID 19853504, compound

HRID 1723305Notes

Reaction equation

HRID 1723305 reaction equation
[OH-].[K+].[SH:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)=[N:7][N:8]=1.[I-].[K+].[F:17][CH2:18][F:19]>O.O1CCOCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:17][CH:18]([F:19])[S:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)=[N:7][N:8]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 6345DifluoromethaneHCID 14797Potassium HydroxideHCID 178527964HCID 178527964, compound

Product 1

HCID 19853504HCID 19853504, compoundYield 4,223.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6.2 g of 85% potassium hydroxide in 18 ml of water is added a solution of 6 g (0.03 mol) of 2-mercapto-5-pyrazin-2-yl-1,3,4-thiadiazole in 90 ml of dioxane. Then 0.2 g of potassium iodide and 0.2 g of tetrabutylammonium bromide are added to the reaction mixture and 13 g of gaseous difluoromethane are introduced over 6 hours at 22° to 37° C. After evaporating off the dioxane, the reaction mixture is diluted with ethyl acetate, the aqueous phase is separated and the organic solution is washed cold with 1N sodium hydroxide solution and water, dried over sodium sulfate and clarified with activated carbon. The ethyl acetate is removed under vacuum and the residue is crystallised from ethyl acetate/hexane, affording 312 g (43%) of the title compound with a melting point of 113°-115° C.

Workup

  1. additionare introduced over 6 hours at 22° to 37° C
  2. customAfter evaporating off the dioxane
  3. additionthe reaction mixture is diluted with ethyl acetate
  4. customthe aqueous phase is separated
  5. washthe organic solution is washed cold with 1N sodium hydroxide solution and water
  6. dry with materialdried over sodium sulfate
  7. customThe ethyl acetate is removed under vacuum
  8. customthe residue is crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-88c025a36da54238bac2a6943dcdec58
Source dataset
uspto-grants-1989_08
Patent number
US04861367

Reaction notes

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