m-Chloroperbenzoic acid → 4'-Acetyl-2'-(2,4-difluorophenylsulfinyl)methanesulfonanilide

HRID 1087211Notes

Reaction equation

HRID 1087211 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([C:15]1[CH:25]=[CH:24][C:18]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:17]([S:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[F:34])[CH:16]=1)(=[O:14])[CH3:13]>ClCCl>[C:12]([C:15]1[CH:25]=[CH:24][C:18]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:17]([S:26]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[F:34])=[O:9])[CH:16]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10450972Methanesulfonamide, N-[4-acetyl-2-[(2,4-difluorophenyl)thio]phenyl]-

Product 1

HCID 100448564'-Acetyl-2'-(2,4-difluorophenylsulfinyl)methanesulfonanilideYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (80%; 0.76 g) in dichloromethane (12 ml) was added dropwise to a stirred solution of 4'-acetyl-2'-(2,4-difluorophenylthio)methanesulfonanilide (1.2 g) in dichloromethane (12 ml) at 5° to 10° C. The solution was stirred for 1 hour at the same temperature, washed with a saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate, and concentrated. The oily residue (0.9 g) was crystallized from ethanol to give crystals of 4'-acetyl-2'-(2,4-difluorophenylsulfinyl)methanesulfonanilide (0.73 g).

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe oily residue (0.9 g) was crystallized from ethanol

Sources & evidence

ORD record
ord-faf730fda6434290a99f6eac47740265
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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