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Pyridine → 4-[(ethylsulfonyl)amino]benzoic acid

HRID 2073722
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HRID 2073722 반응식
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:19]([S:21](Cl)(=[O:23])=[O:22])[CH3:20]>C(Cl)Cl>[CH2:19]([S:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)(=[O:23])=[O:22])[CH3:20]
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 2337BenzocaineHCID 11667Ethanesulfonyl chloride

생성물 1

HCID 15162614-[(ethylsulfonyl)amino]benzoic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

To a solution of 16.5 g (0.1 mol) of ethyl 4-aminobenzoate and 16 g (0.2 mol) of pyridine in 200 mL of methylene chloride cooled to 0° C. add dropwise 13 g (0.1 mol) of ethanesulfonyl chloride. After the addition is complete stir the mixture at 20° C. for 4 hr. After this time extract the mixture with three 100 mL portions of 1N sodium hydroxide. Heat the basic extracts at reflux for 2 hr, cool to 0°-10° C. and carefully add 60 mL of concentrated hydrochloric acid. Collect the resulting precipitate to obtain the title compound.

후처리

  1. additionAfter the addition
  2. extractionAfter this time extract the mixture with three 100 mL portions of 1N sodium hydroxide
  3. temperatureHeat the basic extracts
  4. temperatureat reflux for 2 hr
  5. temperaturecool to 0°-10° C.
  6. customCollect the resulting precipitate

출처 및 근거

ORD 기록
ord-6ef24752c0274e68a2327c7ab7d2974a
출처 데이터셋
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04920116

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