Benzocaine → HCID 692488, compound

HRID 485246Notes

Reaction equation

HRID 485246 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8](Cl)=[O:9])=[CH:4][CH:3]=1.ClCCl.[NH2:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1>O>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 6344Dichloromethane2×HCID 534112944-Chlorocinnamoyl chloride

Product 1

HCID 692488HCID 692488, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 21.8 g. of p-chlorocinnamoyl chloride is dissolved in 250 ml. of dichloromethane. To this is added, with stirring, a solution of 35.7 g. of ethyl 4-aminobenzoate in 250 ml. of dichlormethane. The mixture is stirred overnight, then 300 ml. of water are added, stirring is continued for 30 minutes, and the solid is collected by filtration and dried. This solid is boiled in 600 ml. of ethanol and 100 ml. of chloroform, filtered, and the volume reduced to 450 ml., giving a solid, 15.0 g. of which is recrystallized from a mixture of 800 ml. of ethanol and 250 ml. of chloroform by boiling to a volume of 250 ml., giving 13.57 g. of the desired product as off-white crystals, m.p. 203°-204° C.

Workup

  1. additionTo this is added
  2. stirringThe mixture is stirred overnight
  3. stirringstirring
  4. filtrationthe solid is collected by filtration
  5. customdried
  6. filtrationof chloroform, filtered
  7. custom, giving a solid, 15.0 g
  8. customof which is recrystallized from a mixture of 800 ml
  9. custom, giving 13.57 g

Sources & evidence

ORD record
ord-70f29a74f304477f9293cf68cc44f51f
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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