Methylmercaptan sodium → 2-[(Methylthio)methyl]-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole
Reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=4)[C:12]=3[CH:27]=2)=[N:6][N:7]=1.[CH3:28][SH:29].[Na]>O1CCCC1.C(OCC)(=O)C>[CH3:28][S:29][CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=4)[C:12]=3[CH:27]=2)=[N:6][N:7]=1Participants
5
Procedure
A solution of 2-(chloromethyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (1.40 g, 3.55 mmol) and sodium methyl mercaptan (95%, 0.42 g, 5.67 mmol) in tetrahydrofuran (15 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) and recrystallized from hexane/diisopropyl ether to give the title compound (1.12 g, yield 78%) as colorless crystals.
Workup
- washwashed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)
- customrecrystallized from hexane/diisopropyl ether
Sources & evidence
- ORD record
- ord-463cd66f8039497698642dccf8d79e12
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492378B2
Reaction notes
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