Phenylacetyl chloride → N-(3-chloro-alpha,alpha-dimethylbenzyl)-N-(2-oxopropyl)phenylacetamide

HRID 1461654Notes

Reaction equation

HRID 1461654 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([NH:8][CH2:9][C:10](=[O:12])[CH3:11])([CH3:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[C:22]1([CH2:28][C:29](Cl)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([N:8]([CH2:9][C:10](=[O:12])[CH3:11])[C:29](=[O:30])[CH2:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 11430Potassium CarbonateHCID 157541571-(3-Chloro-alpha,alpha-dimethylbenzylamino)-2-propanone

Product 1

HCID 15754160N-(3-chloro-alpha,alpha-dimethylbenzyl)-N-(2-oxopropyl)phenylacetamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

22.6 g (0.1 mol) of 1-(3-chloro-α,α-dimethylbenzylamino)-2-propanone prepared by the method of Reference Example 5, was dissolved in 200 ml of acetone, and 14.0 g (0.11 mol) of potassium carbonate was added thereto. The mixture was cooled with ice water, and then 15.5 g (0.1 mol) of phenylacetyl chloride was gradually dropwise added thereto under stirring. After completion of the dropwise addition, the reaction mixture was returned to room temperature and stirred for 3 hours. Then, the solvent was distilled off under reduced pressure, and then water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was crystallized from n-hexane to obtain 21.5 g (yield: 62.5%) of the desired compound.

Workup

  1. additionAfter completion of the dropwise addition
  2. customwas returned to room temperature
  3. stirringstirred for 3 hours
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. additionwater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-757fbc4ce4e641819342b769207bca63
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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