Antimony trichloride → 2-[3-[4-[(Fluoromethyl)thio]phenyl]-1-benzofuran-5-yl]-5-methyl-1,3,4-oxadiazole

HRID 452782

반응식

HRID 452782 반응식
COCCN(S(F)(F)[F:11])CCOC.[CH3:14][C:15]1[O:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[O:27][CH:26]=[C:25]([C:28]4[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[CH:30][CH:29]=4)[C:24]=3[CH:36]=2)=[N:18][N:19]=1.[Sb](Cl)(Cl)Cl>ClCCl.C(OCC)(=O)C>[F:11][CH2:35][S:34][C:31]1[CH:30]=[CH:29][C:28]([C:25]2[C:24]3[CH:36]=[C:20]([C:17]4[O:16][C:15]([CH3:14])=[N:19][N:18]=4)[CH:21]=[CH:22][C:23]=3[O:27][CH:26]=2)=[CH:33][CH:32]=1

참가 물질

6

반응물 3

HCID 24814Antimony trichlorideHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 444817562-Methyl-5-[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

생성물 1

HCID 686639622-[3-[4-[(Fluoromethyl)thio]phenyl]-1-benzofuran-5-yl]-5-methyl-1,3,4-oxadiazole수율 30.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of [bis(2-methoxyethyl)amino]sulfur trifluoride (1.38 mL, 7.50 mmol) in dichloromethane (10 mL) was added dropwise a solution of 2-methyl-5-[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (1.61 g, 5.00 mmol) in dichloromethane (15 mL) at room temperature. Antimony (III) chloride (0.0570 g, 0.250 mmol) was added to the solution, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/tetrahydrofuran=1/1) and recrystallized from hexane/ethyl acetate to give the title compound (517 mg, yield 30%) as pale-yellow crystals.

후처리

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/tetrahydrofuran=1/1)
  5. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-f89e108746f840ab95f83b7d38c22bb8
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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