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

HRID 58123

Reaction equation

HRID 58123 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([NH:11][C:12](=[O:14])[CH3:13])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 663013,5-Dimethoxyaniline

Product 1

HCID 702039N-(3,5-dimethoxyphenyl)acetamideYield 90,486%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,5-dimethoxy-phenylamine (20 g, 0.131 mol) in toluene (110 mL) was added acetic anhydride (14 g, 0.137 mmol) at room temperature. The resulting mixture was stirred for 18 hours at room temperature. PE (55 mL) was added, the precipitate was filtered and washed with PE (100 mL) to obtain the title compound (24.2 g, yield: 95%). 1H-NMR (400 MHz, CDCl3) δ 2.16 (s, 3H), 3.77 (s, 6H), 6.23 (s, 1H), 6.75 (s, 2H), 7.20 (s, 1H).

Workup

  1. additionPE (55 mL) was added
  2. filtrationthe precipitate was filtered
  3. washwashed with PE (100 mL)

Sources & evidence

ORD record
ord-7e9f9581dfb944339b040643ad69ba60
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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