Potassium Iodide → HCID 20186065, compound

HRID 2309199Notes

Reaction equation

HRID 2309199 reaction equation
[SH:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[N:5][N:6]=1.[OH-].[K+].[I-].[K+].Cl[CH:19]([F:21])[F:20]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[F:20][CH:19]([F:21])[S:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[N:5][N:6]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 6372ChlorodifluoromethaneHCID 14797Potassium HydroxideHCID 178527947HCID 178527947, compound

Product 1

HCID 20186065HCID 20186065, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

6.9 g of 2-mercapto-5-(4'-chlorophenyl)-1,3,4-thiadiazole and 60 ml fo dioxane are added to a solution of 2.4 g of potassium hydroxide in 10 ml of water. After the addition of 0.2 g of potassium iodide and 2 crystals of tetrabutylammonium bromide, the mixture is heated to 40° C. With stirring, a weak stream of chlorodifluoromethane is then passed through the mixture for 4 hours. The reaction mixture is then subsequently concentrated by evaporation in vacuo. The residue remaining after evaporation is taken up in methylene chloride, and the resultant solution is washed in succession with water and 1n sodium hydroxide solution. The solvent is evaporated off, affording the title compound (recrystallised from isopropanol) in the form of colourless crystals with a melting point of 74°-76° C.

Workup

  1. concentrationThe reaction mixture is then subsequently concentrated by evaporation in vacuo
  2. customafter evaporation
  3. washthe resultant solution is washed in succession with water and 1n sodium hydroxide solution
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-3067c592544b4525a085c6e4e6ce449b
Source dataset
uspto-grants-1987_09
Patent number
US04694014

Reaction notes

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