Dichloromethane → N-[(5-acetyl-2-chlorophenyl)methyl]acetamide

HRID 2053659Notes

Reaction equation

HRID 2053659 reaction equation
ClCCl.[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][NH:12][C:13](=[O:15])[CH3:14].[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>O>[C:16]([C:8]1[CH:9]=[CH:10][C:5]([Cl:4])=[C:6]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])[CH:7]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 4626868N-[(2-chlorophenyl)methyl]acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11858678N-[(5-acetyl-2-chlorophenyl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 169.9 kg of the dichloromethane solution of N-[(2-chlorophenyl)methyl]acetamide obtained in Example 3-(A), 47.1 kg (0.6 moles) of acetyl chloride was added and 108.0 kg (0.81 kmoles) of aluminum chloride was added at 15 to 30° C. over 1.5 hours. After dichloromethane was distilled off was distilled off under normal pressure until the temperature reaches 50° C. over 2 hours, the mixture was aged for 6 hours (objective product: other position isomers=76.75%:1.65%; GC area %). After the completion of the reaction, the resulting solution was added dropwise to 450 kg of water at 15 to 35° C. over 2 hours. The solution was extracted twice with 90 kg of dichloromethane and 40 kg of dichloromethane to obtain 199.8 kg of a dichloromethane solution of N-[(5-acetyl-2-chlorophenyl)methyl]acetamide.

Workup

  1. distillationAfter dichloromethane was distilled off
  2. distillationwas distilled off under normal pressure until the temperature
  3. waitthe mixture was aged for 6 hours
  4. customAfter the completion of the reaction
  5. extractionThe solution was extracted twice with 90 kg of dichloromethane and 40 kg of dichloromethane

Sources & evidence

ORD record
ord-cdc0a75fb4a34b5e8d9470ddddcf1625
Source dataset
uspto-grants-2008_02
Patent number
US07326813B2

Reaction notes

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