Acetyl chloride → N-(4-Fluorobenzyl)acetamide

HRID 392832Notes

Reaction equation

HRID 392832 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[C:15](Cl)(=[O:17])[CH3:16]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:15](=[O:17])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 673264-FluorobenzylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 3532104N-(4-Fluorobenzyl)acetamideYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzylamine (11.4 g, 91 mmol) was dissolved in 910 mL of CH2Cl2. To this was added 910 mL of satd NaHCO3 followed by acetyl chloride (23.4 mL, 329 mmol) stir 1 h. The organic layer was separated, washed with satd NaCl, dried over Na2SO4, filtered and solvent removed to yield 8.4 grams of N-(4-fluoro-benzyl)-acetamide.

Workup

  1. customThe organic layer was separated
  2. washwashed with satd NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customsolvent removed

Sources & evidence

ORD record
ord-8cb01639963c4ecd89b7ea6016239016
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

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