Aniline → 3-methoxy-N-phenylbenzamide

HRID 618000Notes

Reaction equation

HRID 618000 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14]>C(N(CC)CC)C.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:14]

Participants

6

Reactant 2

HCID 6115AnilineHCID 74374m-Anisoyl chloride

Product 1

HCID 8353303-methoxy-N-phenylbenzamideYield 95%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 13.4 mL (147 mmol) of aniline in 30.7 mL of triethylamine was slowly added to a solution containing 25.1 g (147 mmol) of 3-methoxybenzoyl chloride in methylene chloride. The resulting reaction mixture was reacted for approximately thirty minutes and then diluted with 1N sodium bicarbonate. The resultant layers were separated and the organic layer was washed sequentially with water, 1M sodium hydroxide and then brine, dried over sodium sulfate, filtered and then reduced to dryness under reduced pressure to provide 31.6 g of an off-white solid.

Workup

  1. customThe resulting reaction mixture
  2. customwas reacted for approximately thirty minutes
  3. customThe resultant layers were separated
  4. washthe organic layer was washed sequentially with water, 1M sodium hydroxide
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8576264157d84e4aa4995e63149e8e7f
Source dataset
uspto-grants-1999_09
Patent number
US05952343

Reaction notes

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