Sodium Sulfite → 1-[4-(Methylsulphinyl)benzenesulphonyl]-2-pyrrolidinone

HRID 981244Notes

Reaction equation

HRID 981244 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])(=[O:22])=[O:21])=[CH:16][CH:15]=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:12][S:13]([C:14]1[CH:15]=[CH:16][C:17]([S:20]([N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])(=[O:22])=[O:21])=[CH:18][CH:19]=1)=[O:9]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19810994HCID 19810994, compound

Product 1

HCID 198110131-[4-(Methylsulphinyl)benzenesulphonyl]-2-pyrrolidinoneYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution containing 2.41 g of m-chloroperbenzoic acid in 48 cm3 of methylene chloride is added to 3.4 g of 1-(4-methylthiobenzene-sulphonyl)pyrrolidin-2-one prepared as in Example 4 in solution in 34 cm3 of methylene chloride, at a temperature not exceeding 25° C. After agitation at ambient temperature for 30 minutes, the reaction medium is then treated with a 10% aqueous solution of sodium sulphite. The organic phase is separated off, washed with a 5% aqueous solution of sodium bicarbonate, then with water. After drying, the solvent is evaporated off under reduced pressure, and the residue is crystallized from 95% ethanol. 1.70 g of expected product is obtained.

Workup

  1. customexceeding 25° C
  2. customThe organic phase is separated off
  3. washwashed with a 5% aqueous solution of sodium bicarbonate
  4. customAfter drying
  5. customthe solvent is evaporated off under reduced pressure
  6. customthe residue is crystallized from 95% ethanol

Sources & evidence

ORD record
ord-4184941a25564006b00cd665140917b7
Source dataset
uspto-grants-1991_02
Patent number
US04990531

Reaction notes

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