Benzocaine → HCID 67441424, compound

HRID 2045291Notes

Reaction equation

HRID 2045291 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]=[CH:16][C:17]([CH3:22])=[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]([F:13])[CH:15]=[CH:16][C:17]=2[CH3:22])=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 27590125-Fluoro-2-methylbenzaldehyde

Product 1

HCID 67441424HCID 67441424, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-benzoic acid ethyl ester (1.65 g, 10 mmol) and 5-fluoro-2-methyl-benzaldehyde (1.38 g, 10 mmol) in ethanol (10 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-(5-fluoro-2-methyl-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (2.0 g, 70%) as a white solid: LC/MS m/e calcd for C17H16FNO2 (M+H)+: 285.3, observed: 286.3.

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-fe36ea9aa1354dc8ae6b3c0059b2a257
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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