Benzocaine → Ethyl 4-(11-bromoundecanamido)benzoate

HRID 648308

Reaction equation

HRID 648308 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13].[NH2:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=1)=[O:13]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 85202Undecanoyl chloride, 11-bromo-

Product 1

HCID 20482534Ethyl 4-(11-bromoundecanamido)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 28 g. of 11-bromoundecanoyl chloride in 100 ml. of methylene chloride is slowly added with stirring to a solution of 20 g. of ethyl 4-aminobenzoate in 100 ml. of methylene chloride. The mixture is filtered and the filtrate is washed with dilute hydrochloric acid and water, dried, and evaporated. Crystallization from acetonitrile affords ethyl 4-(11-bromoundecanamido)benzoate as a white solid.

Workup

  1. filtrationThe mixture is filtered
  2. washthe filtrate is washed with dilute hydrochloric acid and water
  3. customdried
  4. customevaporated
  5. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-20f34d8549964dabaceca69620caa7f5
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Linked notes

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