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

HRID 1087222ノート

反応式

HRID 1087222 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1049Pyridine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-73566f6c54e14f18bc05c20828ae90f6
出典データセット
uspto-grants-1991_07
特許番号
US05034417

反応ノート

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