Benzocaine → 4-(p-Methylhydrocinnamamido)benzoic acid, ethyl ester

HRID 485249Notes

Reaction equation

HRID 485249 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](Cl)=[O:11])=[CH:4][CH:3]=1.[CH3:13][CH2:14][O:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)=[O:17].C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:24][C:21]2[CH:20]=[CH:19][C:18]([C:16]([O:15][CH2:14][CH3:13])=[O:17])=[CH:23][CH:22]=2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 130292003-(4-Methylphenyl)propanoyl chloride

Product 1

HCID 135034334-(p-Methylhydrocinnamamido)benzoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 15 g. of 3-(4-methylphenyl)propionyl chloride in 100 ml. of dichloromethane is created with stirring with a solution of 15 g. of benzocaine and 9.13 g. of triethylamine in 100 ml. of dichloromethane. The mixture is stirred overnight, then washed with 100 ml. each of 10% hydrochloric acid, water, and brine, then dried with magnesium sulfate, and evaporated to yield a solid. This solid is crystallized from 200 ml. of acetonitrile and dried in vacuo, giving 22.08 g. of the desired product, m.p. 154°-155° C.

Workup

  1. stirringThe mixture is stirred overnight
  2. washwashed with 100 ml
  3. dry with materialeach of 10% hydrochloric acid, water, and brine, then dried with magnesium sulfate
  4. customevaporated
  5. customto yield a solid
  6. customThis solid is crystallized from 200 ml
  7. dry with materialof acetonitrile and dried in vacuo
  8. customgiving 22.08 g

Sources & evidence

ORD record
ord-f21ca316d36f4c8ea1299db00f516a54
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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