Dimethylformamide → 6-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]nicotinonitrile

HRID 1294203Notes

Reaction equation

HRID 1294203 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:13])=[C:9]([CH2:11][OH:12])[N:10]=1.Cl[C:15]1[N:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1.CN(C)C=O.[H-].[Na+]>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:13])=[C:9]([CH2:11][O:12][C:15]2[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=2)[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 178612042-(2-Furyl)-5-methyl-4-oxazolylmethanol

Product 1

HCID 688859936-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]nicotinonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of [2-(2-furyl)-5-methyl-4-oxazolyl]methanol (5.18 g), 6-chloro-3-cyanopyridine (4.00 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 1.27 g) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (6.97 g, 86%) of 6-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]nicotinonitrile from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 105-106° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-70d7db180b524d0b836d6fa290b4e6e6
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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