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

HRID 2045277Notes

Reaction equation

HRID 2045277 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]([Cl: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:17][C:16]2[CH:19]=[C:20]([Cl:22])[CH:21]=[C:14]([Br:13])[CH:15]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 177509523-Bromo-5-chlorobenzaldehyde

Product 1

HCID 674412214-{[1-(3-Bromo-5-chloro-phenyl)-methylidene]-amino}-benzoic acid ethyl esterYield 35%

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-chloro-benzaldehyde (11.0 g, 50.3 mmol) in ethanol (100 mL) 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-chloro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (6.4 g, 35%) as a white solid: LC/MS m/e calcd for C16H13BrClNO2 M+: 366.6, observed: 366.6.

Workup

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

Sources & evidence

ORD record
ord-686f0ed52d424e34ae223abf0e2e0ad9
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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