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

HRID 1607688Notes

Reaction equation

HRID 1607688 reaction equation
[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]([O: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[O: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:12])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 164009FK 3311HCID 4311764Sodium borohydride

Product 1

HCID 104501152'-(2,4-Difluorophenoxy)-4'-(1-hydroxyethyl)methanesulfonanilideYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.18 g) was added portionwise to a solution of 4'-acetyl-2'-(2,4-difluorophenoxy)methanesulfonanilide (1.34 g) in methanol (25 ml) at room temperature. The mixture was stirred for 30 minutes, treated with acetic acid (1 ml), and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with an aqueous solution of sodium bicarbonate, and dried over magnesium sulfate. The ethyl acetate layer was evaporated to dryness and the residue was recrystallized from a mixture of ethanol and water to give pale yellow prisms of 2'-(2,4-difluorophenoxy)-4'-(1-hydroxyethyl)methanesulfonanilide (0.97 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with an aqueous solution of sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customThe ethyl acetate layer was evaporated to dryness
  6. customthe residue was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-96d5aad6da4847ceb9cffe7a535a1399
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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