Benzocaine → Ethyl 4-({[4-(benzyloxy)phenyl]methyl}amino)benzoate

HRID 1703079Notes

Reaction equation

HRID 1703079 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.[CH2:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)=[CH:27][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 13079673Ethyl 4-({[4-(benzyloxy)phenyl]methyl}amino)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 16.5 g. of ethyl p-aminobenzoate, 11.64 g. of p-benzyloxybenzyl chloride and 50 ml. of hexamethylphosphoramide are heated in an oil bath at 110° C. for 20 hours. The mixture is chilled, diluted with 25 ml. of water, chilled and the solid mass diluted with additional water in order to filter. The solid is washed with water and recrystallized from ethanol to give off-white crystals, m.p. 144°-146° C. A sample is recrystallized from ethanol to give off-white crystals, m.p. 146°-147° C.

Workup

  1. additionA mixture of 16.5 g
  2. temperatureThe mixture is chilled
  3. additiondiluted with 25 ml
  4. filtrationto filter
  5. washThe solid is washed with water
  6. customrecrystallized from ethanol
  7. customto give off-white crystals, m.p. 144°-146° C
  8. customA sample is recrystallized from ethanol
  9. customto give off-white crystals, m.p. 146°-147° C.

Sources & evidence

ORD record
ord-1ccf138fe96e4f3db325df4498db8763
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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