Chloroacetone → HCID 86659877, compound

HRID 2360156Notes

Reaction equation

HRID 2360156 reaction equation
[CH2:1]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[Li+].C([O-])(O)=O.[Na+].Cl[CH2:25][C:26](=[O:28])[CH3:27]>C(O)C.O>[CH2:1]([N:8]([CH2:25][C:26](=[O:28])[CH3:27])[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6571ChloroacetoneHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 519413N-Benzyl-4-methoxyaniline

Product 1

HCID 86659877HCID 86659877, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-benzyl-p-anisidine (2.00 g, 9.38 mmol) in 19 mL of ethanol was added lithium bromide (1.22 g, 14.0 mmol), NaHCO3 (1.58 g, 18.8 mmol), chloroacetone (0.87 mL, 10.8 mmol) at room temperature, successively. After the reaction mixture was stirred at 80° C. for 3 h, the reaction mixture was added water, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound (2.09 g, 83%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-37920d477bce4630befd9155b2a8b7b7
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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