Benzocaine → Ethyl 4-{[3-(2-methoxyphenyl)propyl]amino}benzoate

HRID 1703099

Reaction equation

HRID 1703099 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24].CN(C)P(N(C)C)(N(C)C)=O>O>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][CH2:15][CH2:14][NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 2552871-(3-Bromopropyl)-2-methoxybenzene

Product 1

HCID 13079682Ethyl 4-{[3-(2-methoxyphenyl)propyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.5 g. of ethyl p-aminobenzoate, 10 g. of 1-bromo-3-(o-methoxyphenyl)propane and 50 ml. of hexamethylphosphoramide is heated at 130° C. for 15 hours, cooled and diluted with 20 ml. of water. The mixture is chilled, diluted with 50 ml. of cold ethanol:H2O (1:1) and filtered. The solid is washed with three 50 ml. portions of cold ethanol-water (1:1) and with water to give crystals, m.p. 106°-109° C. Recrystallization from ethanol (100 ml.) gives yellow crystals, m.p. 111°-113° C.

Workup

  1. additionA mixture of 14.5 g
  2. temperaturecooled
  3. additiondiluted with 20 ml
  4. temperatureThe mixture is chilled
  5. additiondiluted with 50 ml
  6. filtrationof cold ethanol:H2O (1:1) and filtered
  7. washThe solid is washed with three 50 ml
  8. customportions of cold ethanol-water (1:1) and with water to give crystals, m.p. 106°-109° C
  9. customRecrystallization from ethanol (100 ml.)
  10. customgives yellow crystals, m.p. 111°-113° C.

Sources & evidence

ORD record
ord-50cb577dd3e04d71b5730375cf00ce2b
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Linked notes

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