Acetic Anhydride → N-(3,5-dimethoxyphenyl)acetamide

HRID 409657

Reaction equation

HRID 409657 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[NH2:13]>C1(C)C=CC=CC=1.CCCCCC>[CH3:18][O:17][C:15]1[CH:14]=[C:12]([NH:13][C:1](=[O:3])[CH3:2])[CH:11]=[C:10]([O:9][CH3:8])[CH:16]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 663013,5-Dimethoxyaniline

Product 1

HCID 702039N-(3,5-dimethoxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Acetic anhydride (13 ml, 137 mmol, 1.05 equiv) is added (in 15 min) to a suspension of 3,5-dimethoxyaniline (20 g, 131 mmol) in toluene (110 mL), keeping the internal temperature in the range of 35-45° C. The reaction mixture is allowed to stir for 20 h at RT. The resulting thick, grey suspension is diluted with hexane (55 mL) and filtered. The residue in the filter is washed with toluene/Hex (2:1, 70 mL) and Hex, and dried to provide the title compound as a white solid. API-ES-MS: 196.1 [MH]+, tR=3.03 min (purity: 100%, system 1).

Workup

  1. customin the range of 35-45° C
  2. filtrationfiltered
  3. washThe residue in the filter is washed with toluene/Hex (2:1, 70 mL) and Hex
  4. customdried

Sources & evidence

ORD record
ord-b03c433ae0914093abdb6297bd798d96
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Linked notes

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