Acetic Anhydride → Acetamide, N-(3-methoxyphenyl)-

HRID 2393618Notes

Reaction equation

HRID 2393618 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1>C(Cl)Cl>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:23][C:8](=[O:10])[CH3:9])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 108243-Methoxyaniline

Product 1

HCID 11494Acetamide, N-(3-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

120 ml of triethylamine and 56.7 ml of acetic anhydride were added dropwise to a stirred solution of 70.5 g of m-anisidine in 500 ml of a methylene chloride under ice cooling. After completion of the dropwise addition, the reaction mixture was washed and dried, and insolubles were filtered off. The filtrate was concentrated, and the residue was recrystallized from hexane-ethyl acetate to afford 80.9 g of N-(3-methoxyphenyl)acetamide as pale yellow needles. Melting point: 81° to 82° C.

Workup

  1. additionAfter completion of the dropwise addition
  2. washthe reaction mixture was washed
  3. customdried
  4. filtrationinsolubles were filtered off
  5. concentrationThe filtrate was concentrated
  6. customthe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-7efb6f77258d43bbb6260c85d57de67c
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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