Chloroacetyl chloride → N-[2-[4-(2-CHLOROACETYL)PHENYL]ETHYL]ACETAMIDE

HRID 1246448Notes

Reaction equation

HRID 1246448 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[C:10]1([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCCl>[Cl:5][CH2:6][C:7]([C:13]1[CH:14]=[CH:15][C:10]([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])=[CH:11][CH:12]=1)=[O:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 70143N-(2-phenylethyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2468242N-[2-[4-(2-CHLOROACETYL)PHENYL]ETHYL]ACETAMIDEYield 80.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Aluminium chloride (1.63 g) was dissolved in 1,2-dichloroethane (15 mL). Chloroacetylchloride (0. 732 mL) was added to the mixture at 0° C., and stirred additionally for 20 minutes, then N-(2-phenylethyl)acetamide (1 g) in 1,2-dichloroethane (5 mL) was added dropwise. The mixture was stirred for 1 hour at room temperature, and then poured into ice water. The mixture was extracted with chloroform, washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The solid was washed with ethyl acetate and ethyl ether, and dried in vacuo to give N-{2-[4-(2-chloroacetyl)phenyl]ethyl}acetamide as a white powder (1.18 g, 80.4%).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. extractionThe mixture was extracted with chloroform
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe solid was washed with ethyl acetate and ethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a403690cc2bb4df8a6938032e5213f89
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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