Methyl iodide → 2-(Methylthio)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

HRID 452807

반응식

HRID 452807 반응식
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:23][C:22]([SH:24])=[N:21][N:20]=4)[CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.IC.[C:29](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:29][S:24][C:22]1[O:23][C:19]([C:16]2[CH:17]=[CH:18][C:13]3[O:12][CH:11]=[C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:1])([F:25])[F:26])[CH:5]=4)[C:14]=3[CH:15]=2)=[N:20][N:21]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178506378HCID 178506378, 화합물

생성물 1

HCID 686636962-(Methylthio)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole수율 15%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of the obtained 5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole-2-thiol, iodomethane (2.17 mL, 34.8 mmol) and potassium carbonate (3.61 g, 26.1 mmol) in N,N-dimethylformamide (70 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=4/1) and recrystallized from hexane/ethyl acetate to give the title compound (1.01 g, yield 15%) as colorless crystals.

후처리

  1. washwashed twice with water and once with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=4/1)
  5. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-ec52265da39643168b000b1518ec2dcf
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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