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

HRID 1087206ノート

反応式

HRID 1087206 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 100440092'-(2,4-Difluorophenylthio)-4'-(1-hydroxyethyl)methanesulfonanilide収率 66.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-35e2703849444236be7e0c075fc6a32a
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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