Dimethylformamide → N,N-dimethyl-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-amine

HRID 452810Notes

Reaction equation

HRID 452810 reaction equation
Cl.CON.[CH3:5][N:6]([CH3:9])[CH:7]=[O:8].[H-].[Na+].CS(C1O[C:18]([C:21]2[CH:22]=[CH:23][C:24]3[O:28][CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:39])([F:38])[F:37])[CH:30]=4)[C:25]=3[CH:40]=2)=[N:19][N:20]=1)(=O)=O>C(OCC)(=O)C.O1CCCC1>[CH3:5][N:6]([CH3:9])[C:7]1[O:8][C:18]([C:21]2[CH:22]=[CH:23][C:24]3[O:28][CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:37])([F:39])[F:38])[CH:30]=4)[C:25]=3[CH:40]=2)=[N:19][N:20]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 686642352-(Methylsulfonyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

Product 1

HCID 68663422N,N-dimethyl-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazol-2-amineYield 12%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of O-methylhydroxylamine hydrochloride (0.59 g, 7.07 mmol), N,N-dimethylformamide (0.7 mL) and tetrahydrofuran (1.4 mL) was added sodium hydride (60% in oil, 0.31 g, 12.8 mmol) at 0° C., and the resulting mixture was stirred for 15 min. 2-(Methylsulfonyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (0.30 g, 0.71 mmol) was added to the mixture, and the resulting mixture was stirred overnight at room temperature. 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=7/3) and recrystallized from hexane/diisopropyl ether to give the title compound (32.7 mg, yield 12%) as colorless crystals.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=7/3)
  6. customrecrystallized from hexane/diisopropyl ether

Sources & evidence

ORD record
ord-47f9a364809541b4a9ad2f39815b6575
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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