Benzocaine → HCID 67441271, compound

HRID 1801142Notes

Reaction equation

HRID 1801142 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].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[F:22])[CH:17]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[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]=[CH:20][C:21]([F:22])=[C:14]([Cl:13])[CH:15]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2337BenzocaineHCID 5938663-Chloro-4-fluorobenzaldehyde

Product 1

HCID 67441271HCID 67441271, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture solution of 4-amino-benzoic acid ethyl ester (16.5 g, 100 mmol), 3-chloro-4-fluoro-benzaldehyde (16.1 g, 100 mmol) and p-toluenesulfonic acid (384 mg, 2.0 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-[(3-chloro-4-fluoro-benzylidene)-amino]-benzoic acid ethyl ester (30.8 g, quant.) as a pale-white solid: MS calcd. for C16H13ClFNO2 306.74, obsd. (ESI+) [(M+H)+] 306.1.

Workup

  1. temperatureto reflux for 12 hours
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with ether

Sources & evidence

ORD record
ord-3b2c6ba276c644aea045cfc3aad8a287
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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