Benzocaine → HCID 67443124, compound

HRID 2045266Notes

Reaction equation

HRID 2045266 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].[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([F: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:15]=[C:14]([F:13])[CH:21]=[C:20]([F:22])[CH:19]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 5881603,5-Difluorobenzaldehyde

Product 1

HCID 67443124HCID 67443124, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-benzoic acid ethyl ester (3.3 g, 20 mmol) and 3,5-difluoro-benzaldehyde (2.84 g, 20 mmol) in ethanol (50 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-(3,5-difluoro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (4.27 g, 74%) as a white solid: LC/MS m/e calcd for C16H13F2NO2 (M+H)+: 290.3, observed: 290.2.

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-4da66aec808a40578e50d65c5c497722
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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