Acetyl chloride → n-(5-methoxy-2-methylphenyl)acetamide

HRID 536337Notes

Reaction equation

HRID 536337 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:17])=[C:14]([CH:16]=1)[NH2:15].[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:17])=[C:14]([NH:15][C:18](=[O:20])[CH3:19])[CH:16]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 995005-Methoxy-o-toluidine

Product 1

HCID 231720n-(5-methoxy-2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triethylamine (2.9 g, 14.4 mmol) and 5-methoxy-2-methylaniline (1.0 g, 7.2 mmol) in DCM (30 mL) at 0° C., was added acetyl chloride (0.57 g, 7.2 mmol) dropwise. The mixture was stirred at room temperature for 1 hour. The reaction was quenched with saturated ammonium chloride aqueous solution, and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated to give N-(5-methoxy-2-methylphenyl)acetamide as needle-shaped crystals. The crude product was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride aqueous solution
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-627d8e40b7c5452380667d70523e8c98
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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