Benzocaine → 4-{[1-(3-Bromo-5-methyl-phenyl)-methylidene]-amino}-benzoic acid ethyl ester

HRID 2045300Notes

Reaction equation

HRID 2045300 reaction equation
[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].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[CH:17]=O>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:22][C:20]2[CH:19]=[C:16]([CH3:17])[CH:15]=[C:14]([Br:13])[CH:21]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 166410833-Bromo-5-methylbenzaldehyde

Product 1

HCID 674422894-{[1-(3-Bromo-5-methyl-phenyl)-methylidene]-amino}-benzoic acid ethyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-benzoic acid ethyl ester (8.3 g, 50.3 mmol) and 3-bromo-5-methyl-benzaldehyde (11.0 g, 50.3 mmol) in ethanol (100 mL) was prepared. The reaction mixture was heated to reflux for 2 hours. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-{[1-(3-bromo-5-methyl-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (7.3 g, 50%) as a white solid: LC/MS m/e calcd for C17H16BrNO2 M+: 346.2, observed: 346.1.

Workup

  1. customwas prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 2 hours
  4. customThe solvent was removed in vacuo
  5. washthe residue was washed with ether

Sources & evidence

ORD record
ord-4b09e5864e844d1f849f557f6c3c9bf5
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

Loading…