Acetic Acid → HCID 19817741, compound

HRID 1087219Notes

Reaction equation

HRID 1087219 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]([S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH:7]=1)(=[O:5])[CH3:4].C(O)(=O)C>O1CCCC1.CO>[Cl:25][C:19]1[CH:20]=[C:21]([Cl: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]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10318204HCID 10318204, compound

Product 1

HCID 19817741HCID 19817741, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.22 g) was added portionwise to a solution of 4'-acetyl-2'-(2,4-dichlorophenylthio)methanesulfonanilide (1.5 g) in tetrahydrofuran (20 ml) and methanol (10 ml) at room temperature. The mixture was stirred for 9 hours, treated with acetic acid, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with an aqueous solution of sodium bicarbonate, and dried. The solution was evaporated to dryness and the residue was recrystallized from a mixture of ethanol and water to give colorless needles of 2'-(2,4-dichlorophenylthio)-4'-(1-hydroxyethyl)methanesulfonanilide (1.3 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. customdried
  5. customThe solution was evaporated to dryness
  6. customthe residue was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-349c7f739e9c462b8481b50758c85154
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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