Benzocaine → Benzoic acid, p-((3-pyridylmethylene)amino)-, ethyl ester

HRID 1801122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801122
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)[CH3:2]

Komponenten

5

Edukt 2

HCID 2337BenzocaineHCID 103713-Pyridinecarboxaldehyde

Produkt 1

HCID 213269Benzoic acid, p-((3-pyridylmethylene)amino)-, ethyl esterAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-amino-benzoic acid ethyl ester (33 g, 200 mmol), pyridine-3-carbaldehyde (24.0 g, 220 mmol) and p-toluenesulfonic acid (760 mg, 4 mmol) in toluene (600 mL) was heated to reflux for 12 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[(pyridin-3-ylmethylene)-amino]-benzoic acid ethyl ester (51 g, quant.) as a light yellow solid: LC/MS m/e calcd for C15H14N2O2 (M+H)+: 255.29, observed: 255.4.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-9f187d26845445e28266ae432930df55
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344137B2

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