Benzocaine → HCID 690839, compound

HRID 1801042Notes

Reaction equation

HRID 1801042 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:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 707414-Bromobenzaldehyde

Product 1

HCID 690839HCID 690839, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-benzoic acid ethyl ester (4.5 g, 27 mmol) and 4-bromo-benzaldehyde (5.0 g, 27 mmol) in ethanol (150 mL) was prepared. The reaction mixture was heated to reflux for 2 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-{[1-(4-bromo-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (6.3 g, 70%) as a white solid: LC/MS m/e calcd for C16H14BrNO2 M+: 332.2, observed: 332.2, 334.2.

Workup

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

Sources & evidence

ORD record
ord-7583588b2984416ba331c679d0739427
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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