Dimethylformamide → 2-({4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyl}oxy)nicotinonitrile

HRID 1294132Notes

Reaction equation

HRID 1294132 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.Cl[C:24]1[C:29]([C:30]#[N:31])=[CH:28][CH:27]=[CH:26][N:25]=1.CN(C)C=O.[H-].[Na+]>O>[C:30]([C:29]1[C:24]([O:22][CH2:21][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:6][C:2]=3[CH3:1])=[CH:20][CH:19]=2)=[N:25][CH:26]=[CH:27][CH:28]=1)#[N:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 810792-ChloronicotinonitrileHCID 110228074-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

Product 1

HCID 688862202-({4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyl}oxy)nicotinonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of [4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenyl]methanol (10.0 g), 2-chloro-3-cyanopyridine (4.27 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 1.48 g) under ice-cooling. The reaction mixture was stirred at room temperature for 15 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (10.98 g, 90%) of 3-cyano-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]pyridine from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 119-120° C.

Workup

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

Sources & evidence

ORD record
ord-db0a6ecc13c14597ae714ee037494960
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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