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

HRID 485251

Reaction equation

HRID 485251 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](Cl)=[O:10])=[CH:5][CH:4]=1.[CH3:14][CH2:15][O:16][C:17]([C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=1)=[O:18].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:17]([O:16][CH2:15][CH3:14])=[O:18])=[CH:24][CH:23]=2)=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 534017724-Methoxycinnamic acid chloride

Product 1

HCID 7072084-(p-Methoxycinnamamido)benzoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10 g. of p-methoxycinnamoyl chloride in 200 ml. of dichloromethane is slowly added a solution of 0.24 g. of benzocaine and 7.1 ml. of triethylamine in 200 ml. of dichloromethane. The mixture is stirred for 19 hours, then the organic layer is washed with 200 ml. of 10% hydrochloric acid followed by 200 ml. of brine, dried over magnesium sulfate, and condensed to a solid. This solid is crystallized from 100 ml. of ethanol, giving 10.6 g. of the desired product as yellow crystals, m.p. 163°-165.5° C.

Workup

  1. washthe organic layer is washed with 200 ml
  2. dry with materialof brine, dried over magnesium sulfate, and condensed to a solid
  3. customThis solid is crystallized from 100 ml
  4. customof ethanol, giving 10.6 g

Sources & evidence

ORD record
ord-872c52fc9c8a4b789856800578381588
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Linked notes

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