Dimethylformamide → 6-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrile

HRID 1294200Notes

Reaction equation

HRID 1294200 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][OH:14].Cl[C:16]1[N:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.CN(C)C=O.[H-].[Na+]>O>[CH3:1][C:2]1[S: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:16]1[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][N:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 22494033(5-Methyl-2-phenyl-4-thiazolyl)methanol

Product 1

HCID 688845976-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrileYield 74.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (5-methyl-2-phenyl-4-thiazolyl)methanol (5.0 g), 6-chloro-3-cyanopyridine (3.38 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 1.07 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 with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (5.55 g, 74%) of 6-[(5-methyl-2-phenyl-4-thiazolyl)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: 124-125° 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-9869aef00e7048f8a241a9211482b123
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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