Sodium Iodide → 2-Methyl-5-[3-[4-[2-(methylthio)ethoxy]phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

HRID 452785Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)[C:11]=3[CH:22]=2)=[N:4][N:3]=1.Cl[CH2:24][CH2:25][S:26][CH3:27].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:16]=[CH:17][C:18]([O:21][CH2:24][CH2:25][S:26][CH3:27])=[CH:19][CH:20]=4)[C:11]=3[CH:22]=2)=[N:4][N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenol (693 mg, 2.37 mmol), 1-chloro-2-(methylthio)ethane (1.18 mL, 11.9 mmol), sodium iodide (355 mg, 2.37 mmol) and potassium carbonate (1.64 g, 11.9 mmol) in N,N-dimethylformamide (10 mL) was stirred at 90° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and 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=10/1-1/1) and recrystallized from hexane/ethyl acetate to give the title compound (452 mg, yield 52%) as colorless crystals.

Workup

washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-1/1)
customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record: ord-52312987052048b9a7e9555688c86a0e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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