Ethyl Acetate → HCID 12448147, compound

HRID 260004Notes

Reaction equation

HRID 260004 reaction equation
Br[CH2:2][CH:3]([CH2:13]Br)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[OH-].[Na+].C(OCC)(=O)C>ClCCl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:2]=[C:3]1[CH2:13][N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]1=[O:5]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 124481363-Bromo-2-(bromomethyl)-N-phenylpropanamide

Product 1

HCID 12448147HCID 12448147, compoundYield 104.3%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

16.05 g (50 mmol) 3-Bromo-2-bromomethyl-N-phenylpropionamide were dissolved in 250 ml dichloromethane and added to a solution of 30 g sodium hydroxide in 30 ml water. 1.6 g Benzyltriethylammonium chloride were added and the mixture was vigorously stirred for 7 hours. The suspension was then poured on 200 ml ethyl acetate, and the organic phases were separated, washed twice with 150 ml water and dried over magnesium sulfate. Evaporation of the solvent yielded 8.3 g of an oil which was purified by chromatography on silica gel (eluent: dichloromethane). Yield: 8.0 g (100%) M.p. 57°-58° C. Microanalysis: C10H9NO calc. C 75.45 H 5.70 N 8.80 found C 75.06 H 5.76 N 8.71

Workup

  1. customthe organic phases were separated
  2. washwashed twice with 150 ml water
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9e5bab7f6a08409a8ea7be6bf15e2a41
Source dataset
uspto-grants-1996_06
Patent number
US05523400

Reaction notes

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