m-Chloroperbenzoic acid → HCID 70086031, compound

HRID 266437Notes

Reaction equation

HRID 266437 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([S:18]([CH2:20][N:21]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[S:22]2(=[O:24])=[O:23])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([S:18]([CH2:20][N:21]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[S:22]2(=[O:24])=[O:23])(=[O:9])=[O:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70053050HCID 70053050, compound

Product 1

HCID 70086031HCID 70086031, compound

Procedure

A mixture of m-chloroperbenzoic acid (2.2 g, 12.8 mmol) and 2-(phenylsulfinylmethyl) saccharin (3.75 g, 11.6 mmol) in MDC (50 ml) was stirred at room temperature for 2 hours. An additional spatula of peracid was added, and stirring was continued for an additional 1 hour. m-Chlorobenzoic acid was removed by filtration and the solid was washed with a small amount of MDC. The filtrate was washed with sodium bicarbonate solution, dried (Na2SO4) and freed of solvent under vacuum. The resultant solid was recrystallized from 50:50 ethanol:acetonitrile to afford 2-(phenylsulfonylmethyl)saccharin as a white solid, mp 169°-171° C. 1H nmr (90 MHz, DMSO-d6, CDCl3):5.15 (2H, s). FDMS: m/e 196 (M+ -PMT).

Workup

  1. stirringstirring
  2. waitwas continued for an additional 1 hour
  3. customm-Chlorobenzoic acid was removed by filtration
  4. washthe solid was washed with a small amount of MDC
  5. washThe filtrate was washed with sodium bicarbonate solution
  6. dry with materialdried (Na2SO4)
  7. customThe resultant solid was recrystallized from 50:50 ethanol

Sources & evidence

ORD record
ord-08899e593eed4fefab8938c7205c67c5
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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