Water → HCID 66877719, compound

HRID 1014062Notes

Reaction equation

HRID 1014062 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].CN(C1C=CC=CN=1)C.[C:20](Cl)(=[O:23])[CH2:21][CH3:22].O>CC(N(C)C)=O>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C:20](=[O:23])[CH2:21][CH3:22])=[C:3]([C:4]#[N:5])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 62324Propionyl chlorideHCID 800192-Amino-5-chlorobenzonitrile

Product 1

HCID 66877719HCID 66877719, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(Step 1) To a solution of 2-amino-5-chlorobenzonitrile (5.0 g) and dimethylaminopyridine (0.12 g) in dimethylacetamide (25 ml) was added propionyl chloride (3.4 ml) at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into water, and extracted twice 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 recrystallized from ethanol and diisopropyl ether to give N-(4-chloro-2-cyanophenyl)propanamide (5.7 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-13ae6e1f66e848f5ae2bde66310abad8
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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