o-Phenetidine → N-(2-Ethoxyphenyl)-2-methylbenzamide

HRID 1287698

Reaction equation

HRID 1287698 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16])[CH3:12].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CC(C)=O>[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])[CH3:12]

Participants

5

Reactant 3

HCID 7203o-PhenetidineHCID 83732-Methylbenzoic acidHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 576828N-(2-Ethoxyphenyl)-2-methylbenzamideYield 94.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 13.6 g (0.1 mol) portion of o-methylbenzoic acid and 13.7 g of o-ethoxyaniline were dissolved in 200 ml of acetone. A 4.7 g (0.033 mol) amount of phosphorus pentoxide was gradually added to the prepared solution at 30° - 40° C. After the addition, the reaction mixture was refluxed for 3 hours with stirring. The acetone was removed and the residual product was poured into water and was extracted with toluene. The toluene layer was dried over anhydrous sodium sulfate and the toluene was removed to obtain 24.1 g (94.5%) of a clear pink liquid, having a boiling point of 148° C/0.04 mm Hg and nD20 of 1.5929.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was refluxed for 3 hours
  3. customThe acetone was removed
  4. additionthe residual product was poured into water
  5. extractionwas extracted with toluene
  6. dry with materialThe toluene layer was dried over anhydrous sodium sulfate
  7. customthe toluene was removed

Sources & evidence

ORD record
ord-2dacb707b5fd4549a1c468081797601d
Source dataset
uspto-grants-1976_10
Patent number
US03985804

Linked notes

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