Benzocaine → Ethyl 4-(4-acetyl-3-hydroxy-2-propylbenzylamino)benzoate

HRID 1030344Notes

Reaction equation

HRID 1030344 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2].[NH2:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1>C(#N)C>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2337Benzocaine2×HCID 137810224-Acetyl-3-hydroxy-2-propylbenzyl chloride

Product 1

HCID 15682682Ethyl 4-(4-acetyl-3-hydroxy-2-propylbenzylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6.8 g. of 4-acetyl-3-hydroxy-2-propylbenzyl chloride and 14.9 g. of ethyl 4-aminobenzoate in 200 ml. of acetonitrile was heated to reflux for 48 hours. An additional 9.9 g. of ethyl 4-aminobenzoate were added and the reaction was refluxed an additional 120 hours. The reaction mixture was cooled and concentrated in vacuo. The residue was dissolved in methylene chloride. The organic solution was washed first with a saturated sodium carbonate solution and then with water. The organic solution was then dried over sodium sulfate and evaporated to dryness. Chromatography of the residue afforded 7.4 g. of the desired title product. NMR.

Workup

  1. temperatureto reflux for 48 hours
  2. temperaturethe reaction was refluxed an additional 120 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washThe organic solution was washed first with a saturated sodium carbonate solution
  7. dry with materialThe organic solution was then dried over sodium sulfate
  8. customevaporated to dryness
  9. customChromatography of the residue afforded 7.4 g

Sources & evidence

ORD record
ord-992ae5ad7ba243cf9b50981f71f6332f
Source dataset
uspto-grants-1992_04
Patent number
US05105017

Reaction notes

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