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

HRID 1578624

Reaktionsgleichung

Reaktionsgleichung von HRID 1578624
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 576828N-(2-Ethoxyphenyl)-2-methylbenzamideAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-25e01d54eecf47a7a51dac7c93773065
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03937840

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