Acetic Anhydride → N-(2-(4-Methoxyphenyl)ethyl)acetamide

HRID 6753

Reaction equation

HRID 6753 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](NCC)=[CH:5][CH:4]=1.[CH2:12]([N:14](CC)[CH2:15][CH3:16])[CH3:13].C(OC(=O)C)(=[O:21])C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:13][CH2:12][NH:14][C:15](=[O:21])[CH3:16])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11804947N-Ethyl-4-methoxybenzenamine

Product 1

HCID 584258N-(2-(4-Methoxyphenyl)ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-methoxy-phenyl)-ethylamine (10 g, Aldrich, U.S.A.) and triethylamine (10.1 mL) in dichloromethane (200 mL) was added acetic anhydride (7.4 g). The mixture was stirred at rt for 3 h and was washed successively with hydrochloric acid (1 M, 100 mL), 10% aqueous potassium carbonate (100 mL) and brine (100 mL). The dichloromethane layer was dried over sodium sulfate and filtered. The filtrate was evaporated to afford N-[2-(4-methoxy-phenyl)-ethyl]-acetamide (13.0 g).

Workup

  1. washwas washed successively with hydrochloric acid (1 M, 100 mL), 10% aqueous potassium carbonate (100 mL) and brine (100 mL)
  2. dry with materialThe dichloromethane layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-71c59c4825cc4dd98d2a6241a5eac55b
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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