Benzocaine → p-(p-Chlorocinnamamido)benzoic acid, ethyl ester

HRID 485246노트

반응식

HRID 485246 반응식
[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

참가 물질

5

반응물 3

HCID 2337BenzocaineHCID 6344Dichloromethane2회HCID 534112944-Chlorocinnamoyl chloride

생성물 1

HCID 692488p-(p-Chlorocinnamamido)benzoic acid, ethyl ester

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-70f29a74f304477f9293cf68cc44f51f
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536346

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