Acetyl chloride → N-Benzylacetamide

HRID 1282054Notes

Reaction equation

HRID 1282054 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:11](Cl)(=[O:13])[CH3:12]>C(Cl)Cl>[C:2]1([CH2:1][NH:8][C:11](=[O:13])[CH3:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 7504BenzylamineHCID 14798Sodium Hydroxide

Product 1

HCID 11500N-Benzylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzylamine (98.1 g) in methylene chloride (100 ml) was added an aqueous solution (200 ml) of sodium hydroxide (44 g). While further stirring the mixture, acetyl chloride (78 ml) was added at 15-20° C. over 1 hr. This reaction mixture was stirred at room temperature for 30 min and extracted with chloroform (100 ml×2). The chloroform layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a white solid (160 g). The obtained solid was crystallized from hexane: ethyl acetate (2:1, 750 ml) to give the title compound (125.7 g) as white crystals, m.p.=61-62° C.

Workup

  1. additionwas added at 15-20° C. over 1 hr
  2. extractionextracted with chloroform (100 ml×2)
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6b7638f7d6b14299a5321c2937699670
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

Loading…