Water → HCID 68663304, compound

HRID 452837Notes

Reaction equation

HRID 452837 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:16]=[N:17][NH:18][CH:19]=4)[C:11]=3[CH:20]=2)=[N:5][N:6]=1.[CH3:21][O:22][CH2:23]Cl.[H-].[Na+].O>CN(C)C=O>[CH3:21][O:22][CH2:23][N:18]1[CH:19]=[C:15]([C:12]2[C:11]3[CH:20]=[C:7]([C:4]4[O:3][C:2]([CH3:1])=[N:6][N:5]=4)[CH:8]=[CH:9][C:10]=3[O:14][CH:13]=2)[CH:16]=[N:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 68663199HCID 68663199, compound

Product 1

HCID 68663304HCID 68663304, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-5-[3-(1H-pyrazol-4-yl)-1-benzofuran-5-yl]-1,3,4-oxadiazole (213 mg, 0.80 mmol) and (chloromethyl) methyl ether (0.091 mL, 1.2 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% in oil, 60 mg, 1.2 mmol) by small portions at room temperature, and the resulting mixture was stirred for 10 min. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 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=1/1) and crystallized from hexane/ethyl acetate to give the title compound (128 mg, yield 52%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 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=1/1)
  6. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-503594960fea4b4cb9ae9092a82924ca
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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