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

HRID 328626

Reaction equation

HRID 328626 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

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 76908N-(1,1-Dimethylethyl)benzenemethanamine

Product 1

HCID 2386050N-benzyl-N-tert-butyl-2-chloroacetamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. customto reach room temperature
  4. customthe organic layer is separated
  5. washwashed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-5f90d87b76b841d88b04a4c41097ad9d
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Linked notes

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