Benzocaine → Ethyl 4-amino-3-chlorobenzoate

HRID 55223

반응식

HRID 55223 반응식
[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.[Cl:13]N1C(=O)CCC1=O>ClCCl>[Cl:13][C:12]1[CH:11]=[C:5]([CH:4]=[CH:3][C:2]=1[NH2:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

4

반응물 2

HCID 2337BenzocaineHCID 31398Chlorosuccinimide

생성물 1

HCID 1515285Ethyl 4-amino-3-chlorobenzoate수율 73.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 8.26 g of ethyl 4-aminobenzoate, 8.26 g of N-chlorosuccinimide in 50 ml of dichloromethane is refluxed overnight. The mixture is washed with saturated NaHCO3 solution and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated and hexane added. Chilling gives 7.38 g of ethyl 3-chloro-4-aminobenzoate, m.p. 82°-83° C.

후처리

  1. temperatureis refluxed overnight
  2. washThe mixture is washed with saturated NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. washthe filter cake washed with dichloromethane
  5. concentrationThe filtrate is concentrated
  6. additionhexane added
  7. temperatureChilling

출처 및 근거

ORD 기록
ord-6fafba2a6afb4f6683c7f9417e124f59
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624923

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