Aniline → 4-methoxy-N-phenylbenzamide

HRID 2358289Notes

Reaction equation

HRID 2358289 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>C(Cl)Cl>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:1]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 7477p-Anisoyl chlorideHCID 8857Ethyl AcetateHCID 81531Diisopropylethylamine

Product 1

HCID 3460374-methoxy-N-phenylbenzamideYield 25.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Anisoyl chloride (10 g, 58.5 mmol) was dissolved in methylene chloride (500 mL) under argon. Aniline (8.0 mL, 87.7 mmol) was added dropwise with stirring. Diisopropylethylamine (10.0 mL, 58.5 mmol) was added dropwise to give a white suspension. After 3 h the contents of the reaction flask were washed with 5% potassium bisulfate then sat. sodium bicarbonate. The organic portion was dried with sodium sulfate (anh.), filtered and evaporated in vacuo to give a solid. Trituration with ethyl acetate gave the title compound 1 as a white solid (3.37 g, 25%)

Workup

  1. customto give a white suspension
  2. washAfter 3 h the contents of the reaction flask were washed with 5% potassium bisulfate
  3. dry with materialThe organic portion was dried with sodium sulfate (anh.)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a solid

Sources & evidence

ORD record
ord-074119a816744247a84f18ced5fba3eb
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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