Potassium Carbonate → HCID 43093084, compound

HRID 1444380Notes

Reaction equation

HRID 1444380 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]#[N:21]>CC(C)=O>[C:20]([CH2:19][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1)#[N:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 121243-Hydroxyacetanilide

Product 1

HCID 43093084HCID 43093084, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-hydroxy-phenyl)-acetamide (5 g, 33.1 mmol) in acetone (50 ml) were added K2CO3 (5.49 g, 39.8 mmol) and bromo-acetonitrile (4.37 g, 36.4 mmol). The reaction mixture was heated to 100° C. for 3 h, filtered and the acetone layer evaporated in vacuo. This residue was dissolved in EtOAc (100 ml) and washed with 1M NaOH (10 ml×2). The organic layer was dried (Na2SO4), filtered and the solvent removed in vacuo. The crude residue was purified by column chromatography eluting with 80% EtOAc in heptane to give the title compound.

Workup

  1. filtrationfiltered
  2. customthe acetone layer evaporated in vacuo
  3. dissolutionThis residue was dissolved in EtOAc (100 ml)
  4. washwashed with 1M NaOH (10 ml×2)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe crude residue was purified by column chromatography
  9. washeluting with 80% EtOAc in heptane

Sources & evidence

ORD record
ord-34c1dd8d889242c58df91beb3d02d2fb
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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