Acetic Acid → 2'-(2,4-Difluorophenylthio)-4'-(1-hydroxyethyl)methanesulfonanilide

HRID 1087206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087206
[BH4-].[Na+].[C:3]([C:6]1[CH:16]=[CH:15][C:9]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:8]([S:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[CH:7]=1)(=[O:5])[CH3:4].C(O)(=O)C>CO>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[S:17][C:8]1[CH:7]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:16]=[CH:15][C:9]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10450972Methanesulfonamide, N-[4-acetyl-2-[(2,4-difluorophenyl)thio]phenyl]-

Produkt 1

HCID 100440092'-(2,4-Difluorophenylthio)-4'-(1-hydroxyethyl)methanesulfonanilideAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.2 g) was added portionwise to a solution of 4'-acetyl-2'-(2,4-difluorophenylthio)methanesulfonanilide (1.55 g) in methanol (30 ml) at 15° C. The mixture was stirred overnight at room temperature, treated with acetic acid, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with an aqueous solution of sodium bicarbonate, dried, and concentrated. The residual oil (1.6 g) was purified by column chromatography on silica gel (50 g) eluting with a mixture of toluene and ethyl acetate (4:1). The purified product was recrystallized from a mixture of ethanol and water (2:1) to give crystals of 2'-(2,4-difluorophenylthio)-4'-(1-hydroxyethyl)methanesulfonanilide (1.03 g).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with an aqueous solution of sodium bicarbonate
  4. customdried
  5. concentrationconcentrated
  6. customThe residual oil (1.6 g) was purified by column chromatography on silica gel (50 g)
  7. washeluting with a mixture of toluene and ethyl acetate (4:1)
  8. customThe purified product was recrystallized from a mixture of ethanol and water (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-35e2703849444236be7e0c075fc6a32a
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034417

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