Benzocaine → HCID 67440734, compound

HRID 2045271Notes

Reaction equation

HRID 2045271 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]=[CH:16][C:17]([F:22])=[C:18]([CH:21]=1)[CH:19]=O>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:19][C:18]2[CH:21]=[C:14]([Br:13])[CH:15]=[CH:16][C:17]=2[F:22])=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 67440734HCID 67440734, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-benzoic acid ethyl ester (1.65 g, 10 mmol) and 5-bromo-2-fluoro-benzaldehyde (2.03 g, 10 mmol) in ethanol (20 mL) 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-(5-bromo-2-fluoro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (2.76 g, 79%) as a white solid: LC/MS m/e calcd for C16H13BrFNO2 M+: 350.2, observed: 350.1, 352.1.

Workup

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

Sources & evidence

ORD record
ord-6e27200e68254c56b7ac53851b2181e2
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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