Pyridine → N-[(4-Chlorophenyl)methyl]-N-methylacetamide

HRID 648757Notes

Reaction equation

HRID 648757 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][CH3:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.C=C1O[C:20](=[O:21])[CH2:19]1>C1(C)C=CC=CC=1.O>[CH3:8][N:7]([CH2:6][C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:20](=[O:21])[CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 12661DiketeneHCID 66905Benzenemethanamine, 4-chloro-N-methyl-

Product 1

HCID 12633526N-[(4-Chlorophenyl)methyl]-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Dissolved in toluene was 3.1 g (0.02 mole) of 4-chloro-N-methyl-benzylamine, followed by an addition of a catalytic amount of pyridine and a further dropwise addition of 1.8 g (0.022 mole) of diketene at room temperature. After stirring the reaction mixture at room temperature for 3 hours, it was poured in water and then extracted with toluene. Subsequent to purification, N-methyl-N-(4-chlorobenzyl)acetamide was obtained in an oily form.

Workup

  1. extractionextracted with toluene
  2. customSubsequent to purification

Sources & evidence

ORD record
ord-24ea25f346d941ba906ebffb01c3eb53
Source dataset
uspto-grants-1988_04
Patent number
US04736038

Reaction notes

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