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

HRID 1087222Notes

Reaction equation

HRID 1087222 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-73566f6c54e14f18bc05c20828ae90f6
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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