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

HRID 2052484Notes

Reaction equation

HRID 2052484 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-d2b9cf2f497b448dac517f1fbcec1271
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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