Difluoromethane → 2-Difluoromethylthio-5-pyrid-2-yl-1,3,4-thiadiazole

HRID 329943

반응식

HRID 329943 반응식
[SH:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[N:5][N:6]=1.[OH-].[K+].[F:15][CH2:16][F:17]>O1CCOCC1.O.[I-].[K+].[Br-].C([NH+](CCCC)CCCC)CCC>[F:15][CH:16]([F:17])[S:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[N:5][N:6]=1

참가 물질

8

반응물 3

HCID 6345DifluoromethaneHCID 14797Potassium HydroxideHCID 178527949HCID 178527949, 화합물

생성물 1

HCID 198704882-Difluoromethylthio-5-pyrid-2-yl-1,3,4-thiadiazole수율 75.1%

시약·촉매·용매 4

HCID 4875Potassium Iodide촉매HCID 13798051Tributylammonium bromide촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A suspension of 341.5 g (l.75 mol) of 2-mercapto-5-pyrid-2-yl-1,3,4-thiadiazole in 4000 ml of dioxane is added to a solution of 230.5 g of 85% potassium hydroxide in 800 ml of water. Then 10 g of potassium iodide and 6 g of tributylammonium bromide are added to the reaction mixture and 750 g (~8.6 mol) of gaseous difluoromethane are introduced over 41/2 hours at 22°-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 and water, dried over sodium sulfate and clarified with activated carbon. They ethyl acetate is removed under vacuum and the residue is crystallised from ethyl acetate/hexane, affording 321.9 g (75.1%) of the title compound with a melting point of 90°-92° C.

후처리

  1. additionare introduced over 41/2 hours at 22°-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 and water
  6. dry with materialdried over sodium sulfate
  7. customThey ethyl acetate is removed under vacuum
  8. customthe residue is crystallised from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-9ec7e6f0f65c41ab83ae5aecb742d22c
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894380

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