Sodium hydride → N-[3-(Trifluoromethyl)phenyl]-3,3-dimethylazetidin-2-one

HRID 481385Notes

Reaction equation

HRID 481385 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[C:11]([CH2:14]Cl)([CH3:13])[CH3:12])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+]>CN(C)C=O>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:12][C:11]([CH3:14])([CH3:13])[C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 19066381N-[3-(Trifluoromethyl)phenyl]-2-chloromethyl-2-methyl-propionamide

Product 1

HCID 19066383N-[3-(Trifluoromethyl)phenyl]-3,3-dimethylazetidin-2-oneYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

Dissolved in dimethylformamide were 1.4 g of N-[3-(trifluoromethyl) phenyl]-2-chloromethyl-2-methylpropionamide, and 0.24 g of sodium hydride were added with stirring at 5° C. After stirring the mixture at room temperature for 15 hours, it was added with ice water and extracted with diethyl ether. The extract was dried over magnesium sulfate. Diethyl ether was distilled off, and the residue was purified by column chromatography on silica gel to obtain 1.00 g (yield: 82%) of the title compound.

Workup

  1. additionwere added
  2. stirringAfter stirring the mixture at room temperature for 15 hours
  3. extractionextracted with diethyl ether
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationDiethyl ether was distilled off
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4a7e85aecc4b4144bd6e49330f18d2b1
Source dataset
uspto-grants-1998_08
Patent number
US05789419

Reaction notes

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