Ethyl cyanoacetate → 2-cyano-N-(3,4-difluorophenyl)acetamide

HRID 2095868Notes

Reaction equation

HRID 2095868 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[C:10]([CH2:12][C:13](OCC)=[O:14])#[N:11]>C(OCC)(=O)C.O1CCCC1>[C:10]([CH2:12][C:13]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([F:9])=[C:2]([F:1])[CH:3]=1)=[O:14])#[N:11]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 774693,4-Difluoroaniline

Product 1

HCID 45756752-cyano-N-(3,4-difluorophenyl)acetamideYield 56%

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A mixed solution of 3,4-difluoroaniline (10 g, 77.5 mmol) and ethyl cyanoacetate (10.5 g, 92.9 mmol) was heated to 180° C. and stirred for 8 hr. After cooling to room temperature, the mixture was dissolved in ethyl acetate/tetrahydrofuran and washed with water and saturated brine in this order. The mixture was dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (7.6 g, 56%) as a yellow solid.

Workup

  1. washwashed with water and saturated brine in this order
  2. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. washthe obtained residue was washed with ethyl acetate
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-061afb98e84440ccb2661cf1d553125f
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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