Dimethylformamide → 5-Chloro-2-(2-oxo-1,3-oxazolidin-3-yl)benzonitrile

HRID 1015779Notes

Reaction equation

HRID 1015779 reaction equation
[O:1]1[CH2:5][C:4](=O)[N:3]=[C-:2]1.[H-].[Na+].[Cl:9][C:10]1[CH:11]=[CH:12][C:13](F)=[C:14]([CH:17]=1)[C:15]#[N:16].CN(C)C=[O:22]>[Cl-].[Na+].O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([N:3]2[CH2:4][CH2:5][O:1][C:2]2=[O:22])=[C:14]([CH:17]=1)[C:15]#[N:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 936535-Chloro-2-fluorobenzonitrileHCID 532495662H-1,3-oxazol-2-id-4-one

Product 1

HCID 668960965-Chloro-2-(2-oxo-1,3-oxazolidin-3-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

(Step 1) To a solution (of 2-oxazolidone (1.23 g) in N,N-dimethylformamide (20 ml) was added sodium hydride (0.62 g) under ice-cooling, and the mixture was stirred for 5 min. 5-Chloro-2-fluorobenzonitrile (2.0 g) was added, and the mixture was stirred at room temperature for 2 hr. Saturated brine was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give 5-chloro-2-(2-oxo-1,3-oxazolidin-3-yl)benzonitrile (1.8 g) as a white solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b0f9eb6921f54d4391d748845324f4ec
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

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