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Methanesulfonyl chloride → 3-(2,4-Difluorophenylthio)-4-(methanesulfonamido)benzoic acid

HRID 1087212
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HRID 1087212 반응식
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]=1[S:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[S:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[NH:1][S:23]([CH3:22])(=[O:25])=[O:24])[C:6]([OH:8])=[O:7]
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참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 10040979Ethyl 4-amino-3-(2,4-difluorophenylthio)benzoate

생성물 1

HCID 100439883-(2,4-Difluorophenylthio)-4-(methanesulfonamido)benzoic acid수율 51.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
60 °C

실험 절차

A mixture of ethyl 4-amino-3-(2,4-difluorophenylthio)benzoate (1.1 g) and methanesulfonyl chloride (0.93 g) in pyridine (5 ml) was stirred at 60° C. for 2 hours. The reaction mixture was evaporated. The residue was dissolved in methanol and treated with potassium hydroxide (2 g). The mixture was concentrated and the residue was dissolved in water and washed with chloroform. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The solid residue was recrystallized from ethanol to give 3-(2,4-difluorophenylthio)-4-(methanesulfonamido)benzoic acid (0.66 g).

후처리

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in methanol
  3. additiontreated with potassium hydroxide (2 g)
  4. concentrationThe mixture was concentrated
  5. dissolutionthe residue was dissolved in water
  6. washwashed with chloroform
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. customdried
  10. customevaporated
  11. customThe solid residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-fd53285f608047cd85045982a19482a6
출처 데이터셋
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05034417

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