Water → N-[(2-chlorophenyl)methyl]acetamide

HRID 2053658Notes

Reaction equation

HRID 2053658 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH2:9].[C:10](OC(=O)C)(=[O:12])[CH3:11].O.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10](=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 666482-Chlorobenzylamine

Product 1

HCID 4626868N-[(2-chlorophenyl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

42.8 kg (0.3 kmoles) of (2-chlorophenyl)methylamine was dissolved in 118.3 kg of dichloromethane and 32.2 kg (0.315 kmoles) of acetic anhydride was added dropwise at 20 to 40° C. over 1.5 hours, followed by aging at room temperature for 30 minutes. After the completion of the reaction, 60 kg of water was added 55.2 kg of an aqueous 25% sodium hydroxide solution was added dropwise at 20 to 40° C. over 20 minutes. The organic layer was partitioned to obtain 169.9 kg of a dichloromethane solution of N-[(2-chlorophenyl)methyl]acetamide.

Workup

  1. additionwas added dropwise at 20 to 40° C. over 20 minutes
  2. customThe organic layer was partitioned

Sources & evidence

ORD record
ord-ba79cae8debc407f9a6fc6f672466cdf
Source dataset
uspto-grants-2008_02
Patent number
US07326813B2

Reaction notes

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