Benzocaine → Ethyl 4-(benzylamino)benzoate

HRID 1703077Notes

Reaction equation

HRID 1703077 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](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC1C(C)=C(C)C(C)=C(C)C(C)=[C-]PC=1>O>[CH2:13]([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)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 7498Benzyl BromideHCID 131711709HCID 131711709, compound

Product 1

HCID 3832836Ethyl 4-(benzylamino)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.5 g. of ethyl p-aminobenzoate, 8.55 g. of benzyl bromide and 45 ml. of hexamethylphosphorimide are heated in an oil bath at 110° C. for 20 hours. The mixture is diluted with water, chilled, filtered and the solid washed with water to give tan crystals, m.p. 90°-93° C. A sample is recrystallized from ethanol to give tan crystals, m.p. 96°-97° C.

Workup

  1. additionA mixture of 16.5 g
  2. temperaturechilled
  3. filtrationfiltered
  4. washthe solid washed with water
  5. customto give tan crystals, m.p. 90°-93° C
  6. customA sample is recrystallized from ethanol
  7. customto give tan crystals, m.p. 96°-97° C.

Sources & evidence

ORD record
ord-51e41350043f4047b3e37a9f48693096
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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