Phenylacetyl chloride → N-(4-chlorobenzyl)-phenylacetamide

HRID 1384460Notes

Reaction equation

HRID 1384460 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:17][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 660364-Chlorobenzylamine

Product 1

HCID 306763N-(4-chlorobenzyl)-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4.0 g, 25.9 mmol) of phenylacetyl chloride, 3.15 mL (25.9 mmol) of 4-chlorobenzylamine and 5.1 mL of triethylamine in 120 mL of methylene chloride was prepared at 0° C. and then heated to reflux under a nitrogen atmosphere for 18 hours. The solvent was evaporated and the residue was treated with 2 mL of 4-chlorobenzylamine and 3 mL of triethylamine and reheated to reflux overnight. After cooling, the mixture was suspended in 100 mL of methylene chloride, washed with 0.5 N hydrochloric acid, 0.5 N sodium hydroxide and saturated aqueous sodium chloride, followed by drying with magnesium sulfate (MgSO4). The solvent was removed in vacuo to give a white solid which was recrystallized from ethyl acetate:hexane to provide N-(4-chlorobenzyl)-phenylacetamide as a white crystalline solid, 4.15 g (62%).

Workup

  1. customwas prepared at 0° C.
  2. temperatureheated
  3. temperatureto reflux under a nitrogen atmosphere for 18 hours
  4. customThe solvent was evaporated
  5. additionthe residue was treated with 2 mL of 4-chlorobenzylamine and 3 mL of triethylamine
  6. temperatureto reflux overnight
  7. temperatureAfter cooling
  8. washwashed with 0.5 N hydrochloric acid, 0.5 N sodium hydroxide and saturated aqueous sodium chloride
  9. dry with materialby drying with magnesium sulfate (MgSO4)
  10. customThe solvent was removed in vacuo
  11. customto give a white solid which
  12. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-54b2bcbace2a43fc8f663656bd36d85b
Source dataset
uspto-grants-2001_07
Patent number
US06258953B1

Reaction notes

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