Benzocaine → Benzoic acid, 4-[[(4-methoxyphenyl)methyl]amino]-, ethyl ester

HRID 2052486Notes

Reaction equation

HRID 2052486 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.CN(C)P(N(C)C)(N(C)C)=O.Cl[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1>O>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([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

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 4435805Benzoic acid, 4-[[(4-methoxyphenyl)methyl]amino]-, ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33 g. of ethyl p-aminobenzoate, 100 ml. of hexamethylphosphoramide and 15.7 g. of p-(chloromethyl)anisole are heated at 100°-110° C. for 22 hours. The solution is chilled, diluted with 60 ml. of water, chilled, filtered and the solid washed with ethanol and with water to give yellow crystals. Recrystallization from ethanol gives pale yellow crystals, m.p. 128°-130° C.

Workup

  1. additionA mixture of 33 g
  2. temperatureThe solution is chilled
  3. additiondiluted with 60 ml
  4. filtrationfiltered
  5. washthe solid washed with ethanol and with water
  6. customto give yellow crystals
  7. customRecrystallization from ethanol
  8. customgives pale yellow crystals, m.p. 128°-130° C.

Sources & evidence

ORD record
ord-e52b1390bd0c4f1a9c6942d80c55e004
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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