Benzocaine → Ethyl p-{[2-(2,4-dichlorophenoxy)ethyl]amino}benzoate

HRID 2051899Notes

Reaction equation

HRID 2051899 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12].[NH2:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1>CN(C)P(N(C)C)(N(C)C)=O.O>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 2337BenzocaineHCID 1388811-(2-Bromoethoxy)-2,4-dichlorobenzene

Product 1

HCID 20378376Ethyl p-{[2-(2,4-dichlorophenoxy)ethyl]amino}benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 22.8 g of β-bromo-2,4-dichlorophenetole and 29.8 g of ethyl 4-aminobenzoate in 100 ml of hexamethylphosphoramide is heated at 125° C. for 16 hours. The solution is chilled, diluted with water (80 ml) and filtered. The solid is washed with 50% ethanol to give the product. Recrystallization from ethanol gives crystals, mp 111°-113° C.

Workup

  1. temperatureThe solution is chilled
  2. filtrationfiltered
  3. washThe solid is washed with 50% ethanol
  4. customto give the product
  5. customRecrystallization from ethanol
  6. customgives crystals, mp 111°-113° C.

Sources & evidence

ORD record
ord-d571a8a72637411d8ba99361549051b7
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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