Potassium Carbonate → (4,4-Difluorobut-3-enylthio)-3-methyl-1,2,4-thiadiazole

HRID 618198노트

반응식

HRID 618198 반응식
[CH3:1][C:2]1[NH:6][C:5](=[S:7])[S:4][N:3]=1.CC1C=CC(S(O[CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:23][C:22]([F:24])=[CH:21][CH2:20][CH2:19][S:7][C:5]1[S:4][N:3]=[C:2]([CH3:1])[N:6]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 11666101HCID 11666101, 화합물HCID 1784347993-methyl-1,2,4-thiadiazole-5-thiol

생성물 1

HCID 21850474(4,4-Difluorobut-3-enylthio)-3-methyl-1,2,4-thiadiazole수율 32%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 3-methyl-1,2,4-thiadiazole-5(4H)-thione (1.2 g) in acetone (100 cm3) was added 4,4-difluorobut-3-enyl 4-methylbenzenesulfonate (2.4 g) and potassium carbonate (1.2 g) and the mixture was refluxed for 4 hours after which tlc indicated complete consumption of starting material. The reaction was poured into ethyl acetate and water and the layers separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried (MgSO4). The solution of product was then filtered and evaporated under reduced pressure to give a brown oil which was purified by flash chromatography (silica, 7% ethyl acetate in hexane) to give 5-((4,4-difluorobut-3-enylthio)-3-methyl-1,2,4-thiadiazole as a brown oil (0.645 g). M+ =222; 1H NMR: δ2.56(2H, br q); 2.63 (3H,s); 3.30(2H,t); 4.30(1H,m).

후처리

  1. temperaturethe mixture was refluxed for 4 hours after which tlc
  2. customconsumption of starting material
  3. additionThe reaction was poured into ethyl acetate and water
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. filtrationThe solution of product was then filtered
  8. customevaporated under reduced pressure
  9. customto give a brown oil which
  10. customwas purified by flash chromatography (silica, 7% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-c0237b78cb9d4fd1a73d58cf14c585dc
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952359

반응 노트

불러오는 중…