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

HRID 58174

Reaction equation

HRID 58174 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)acetamideYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Acetic anhydride (6.5 mL) was added slowly to a stirred solution of 3,5-dimethoxy aniline (10 g, 65.359 mmol) in toluene (50 mL) under argon atmosphere at room temperature and resulting reaction mixture was stirred for 15 h. After completion of the reaction, reaction was diluted with Hexane and resulted precipitate was collected by filtration and dried under vacuum to afford the title compound (12.5 g, 98% of yield) as a off-white solid. 1HNMR (CDCl3, 300 MHz): δ 7.38 (s, 1H), 6.75 (d, 2H), 6.23 (s, 1H), 3.76 (s, 6H), 2.15 (s, 3H); MS (ESI): 196.1 [M+H]+.

Workup

  1. customresulting
  2. customreaction mixture
  3. customAfter completion of the reaction, reaction
  4. customresulted precipitate
  5. filtrationwas collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-135f662ea86f44bab12e31be80d689b7
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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