Benzocaine → ethyl 4-(decanoylamino)benzoate

HRID 497514Notes

Reaction equation

HRID 497514 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].[C:13](Cl)(=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 66982Decanoyl chloride

Product 1

HCID 289856ethyl 4-(decanoylamino)benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Scheme 3, Compound H) To a solution of 4-amino-benzoic acid ethyl ester (2.0 g, 12.1 mmol) and decanoyl chloride (2.35 g, 13.3 mmol) in methylene chloride (20 mL) was added Et3N (1.34 g, 13.3 mmol). The resultant mixture was stirred at room temperature for one hour and then was diluted with EtOAc, washed by H2O, dried over MgSO4. After filtration and concentration in vacuo, the product was directly used in the next step.

Workup

  1. washwashed by H2O
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration and concentration in vacuo

Sources & evidence

ORD record
ord-145e46e5ae5b4c09842389bf03f8cf55
Source dataset
uspto-grants-2005_09
Patent number
US06949574B2

Reaction notes

Loading…