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

HRID 452782

Reaction equation

HRID 452782 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f89e108746f840ab95f83b7d38c22bb8
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Linked notes

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