Sodium Sulfite → 5-Benzyloxy-3-methylsulfinyl-1,2,4-thiadiazole

HRID 917344Notes

Reaction equation

HRID 917344 reaction equation
[CH2:1]([O:8][C:9]1[S:13][N:12]=[C:11]([S:14][CH3:15])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[S:13][N:12]=[C:11]([S:14]([CH3:15])=[O:24])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 117085115-Benzyloxy-3-methylthio-1,2,4-thiadiazole

Product 1

HCID 230324475-Benzyloxy-3-methylsulfinyl-1,2,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into 12 ml of chloroform was dissolved 1.39 g of 5-benzyloxy-3-methylthio-1,2,4-thiadiazole, and metachloroperbenzoic acid (>70%) was slowly added to the mixture under ice-cooling. After stirring for 1 hour, the compound of low-polarity from the reaction mixture was detected by thin layer chromatography. The reaction mixture was poured into a saturated sodium sulfite aqueous solution, and separated. The organic layer was washed with sodium hydrogen carbonate aqueous solution, dried over anhydrous sodium sulfate, concentrated to give 1.4 g of 5-benzyloxy-3-methylsulfinyl-1,2,4-thiadiazole.

Workup

  1. additionwas slowly added to the mixture under ice-
  2. temperaturecooling
  3. customseparated
  4. washThe organic layer was washed with sodium hydrogen carbonate aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-04ca18a34702406382ef4ef7c318ef5d
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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