Benzocaine → HCID 86600380, compound

HRID 1788570Notes

Reaction equation

HRID 1788570 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].[CH2:13]([O:15][C:16](=[O:26])[CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:14]>C1CCCCC1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:26])=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 7170Ethyl benzoylacetate

Product 1

HCID 86600380HCID 86600380, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

4-Amino-benzoic acid ethyl ester (66 g, 0.4 mol) and 3-oxo-3-phenyl-propionic acid ethyl ester (0.4 mol, 1 eq.) were dissolved in 500 mL cyclohexane and refluxed for 2 days using a Dean-Stark trap. The solution was filtered, the solvent evaporated and the residue recrystallized to give 4-(2-ethoxycarbonyl-1-phenyl-ethylideneamino)-benzoic acid ethyl ester (Compound 481a) MS: 340.18 (M+H+). 4-(2-Ethoxycarbonyl-1-phenyl-ethylideneamino)-benzoic acid ethyl ester was dissolved in diphenyl-methanone (250 mL) and heated to 250° C. for 4 hr. The resulting solution was diluted with diethyl ether and filtered to give 48.6 g of the title intermediate as a white crystalline solid.

Workup

  1. temperaturerefluxed for 2 days
  2. filtrationThe solution was filtered
  3. customthe solvent evaporated
  4. customthe residue recrystallized

Sources & evidence

ORD record
ord-9e7b6eba073f491490bf87ec3ec55f8d
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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