Potassium Hydroxide → 2'-(2,4-Difluorophenylthio)-4'-[2-(methanesulfonamido)-4-thiazolyl]methanesulfonanilide

HRID 1087225Notes

Reaction equation

HRID 1087225 reaction equation
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:18]=[CH:17][C:11]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:10]([S:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[CH:9]=2)[N:7]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].[OH-].[K+]>N1C=CC=CC=1.CO>[F:27][C:21]1[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:20]=1[S:19][C:10]1[CH:9]=[C:8]([C:6]2[N:7]=[C:3]([NH:2][S:29]([CH3:28])(=[O:31])=[O:30])[S:4][CH:5]=2)[CH:18]=[CH:17][C:11]=1[NH:12][S:13]([CH3:16])(=[O:15])=[O:14]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 198177534'-(2-Amino-4-thiazolyl)-2'-(2,4-difluorophenylthio)methanesulfonanilide hydrobromide

Product 1

HCID 104357272'-(2,4-Difluorophenylthio)-4'-[2-(methanesulfonamido)-4-thiazolyl]methanesulfonanilideYield 21.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of 4'-(2-amino-4-thiazolyl)-2'-(2,4-difluorophenylthio)methanesulfonanilide hydrobromide (1.2 g) and methanesulfonyl chloride (0.556 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 evaporated to dryness. The residue (1 g) was purified by column chromatography on silica gel (20 g) eluting with a mixture of toluene and ethyl acetate (1:1) followed by recrystallization from ethanol to give crystals of 2'-(2,4-difluorophenylthio)-4'-[2-(methanesulfonamido)-4-thiazolyl]methanesulfonanilide (0.26 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. customThe extract was evaporated to dryness
  11. customThe residue (1 g) was purified by column chromatography on silica gel (20 g)
  12. washeluting with a mixture of toluene and ethyl acetate (1:1)
  13. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-6d2aa593712a448db02d8d38f98f7904
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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