Potassium Hydroxide → N-ethyl-3-(2,4-difluorophenylthio)-4-(methanesulfonamido)benzamide

HRID 1087222노트

반응식

HRID 1087222 반응식
[CH2:1]([NH:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([S:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[CH:6]=1)[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24].[OH-].[K+]>N1C=CC=CC=1.CO>[CH2:1]([NH:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:23]([CH3:22])(=[O:25])=[O:24])=[C:7]([S:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[CH:6]=1)[CH3:2]

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 10086583N-ethyl4-amino-3-(2,4-difluorophenylthio)benzamide

생성물 1

HCID 10430237N-ethyl-3-(2,4-difluorophenylthio)-4-(methanesulfonamido)benzamide수율 63.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1049Pyridine용매

실험 절차

A mixture of N-ethyl-4-amino-3-(2,4-difluorophenylthio)benzamide (0.84 g) and methanesulfonyl chloride (0.57 g) in pyridine (5 ml) was stirred at room temperature overnight. The reaction mixture was concentrated. The residue was dissolved in ethyl acetate, washed with dilute hydrochloric acid, dried and evaporated. The residue obtained was dissolved in methanol and treated with potassium hydroxide (0.4 g). The solution was concentrated and the residue was dissolved in water. The aqueous solution was acidified with dilute hydrochloric acid and extracted with chloroform. The extract was washed with water, dried, and evaporated. The residual solid was recrystallized from ethanol to give N-ethyl-3-(2,4-difluorophenylthio)-4-(methanesulfonamido)benzamide (0.67 g).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with dilute hydrochloric acid
  4. customdried
  5. customevaporated
  6. customThe residue obtained
  7. concentrationThe solution was concentrated
  8. dissolutionthe residue was dissolved in water
  9. extractionextracted with chloroform
  10. washThe extract was washed with water
  11. customdried
  12. customevaporated
  13. customThe residual solid was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-73566f6c54e14f18bc05c20828ae90f6
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05034417

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