Chloroacetyl chloride → N-benzyl-N-tert-butyl-2-chloroacetamide

Reaction equation

[CH2:1]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>ClCCCl>[CH2:1]([N:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:17](=[O:18])[CH2:16][Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Procedure

To a stirred and cooled mixture of 33 parts of N-benzyl-N-tert.-butylamine in 60 parts of sodium hydroxide solution 20% and 160 parts of 1,2-dichloroethane are added dropwise 34 parts of 2-chloroacetyl chloride at a temperature between -5° and -10° C. Upon completion, stirring is continued at the same temperature for one hour. The reaction mixture is allowed to reach room temperature and the organic layer is separated, washed with water, dried and evaporated, yielding 43 parts of N-benzyl-N-tert.-butyl-2-chloroacetamide as a residue.