Aniline → 4-methoxy-N-phenylbenzamide

HRID 985153Notes

Reaction equation

HRID 985153 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.C(Cl)Cl.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:1]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:10])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 3460374-methoxy-N-phenylbenzamideYield 25.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

p-Anisoyl chloride (10 g, 58.5 mmol) and methylene chloride (500 mL) were combined under Ar. 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 108 as a white solid (3.37 g, 14.8 mmol, 25.4%).

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-aca85f54549743638a169395dfe5b5fa
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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