Benzocaine → Ethyl 4-[(3-phenylprop-2-en-1-yl)amino]benzoate

HRID 1703086Notes

Reaction equation

HRID 1703086 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.Cl[CH2:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[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)[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 53948325Ethyl 4-[(3-phenylprop-2-en-1-yl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33 g. of ethyl p-aminobenzoate 15.3 g. of (3-chloropropenyl)benzene and 80 ml. of hexamethylphosphoramide is heated in an oil bath at 110° C. for 21 hours. The solution is chilled, diluted with 25 ml. of water, chilled, filtered and the solid washed with water to give cream crystals, m.p. 123°-131° C. Recrystallization from ethanol-benzene (9:1) gives pale yellow crystals, m.p. 135°-137° C. Recrystallization from benzene gives white crystals, m.p. 135°-137° C.

Workup

  1. additionA mixture of 33 g
  2. temperatureThe solution is chilled
  3. additiondiluted with 25 ml
  4. filtrationfiltered
  5. washthe solid washed with water
  6. customto give cream crystals, m.p. 123°-131° C
  7. customRecrystallization from ethanol-benzene (9:1)
  8. customgives pale yellow crystals, m.p. 135°-137° C
  9. customRecrystallization from benzene
  10. customgives white crystals, m.p. 135°-137° C.

Sources & evidence

ORD record
ord-5bc49963c8f3494981a5337830a29492
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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