m-Chloroperbenzoic acid → 3-Methylsulfonyl-5-(2-methylcyclohexyl)-1,2,4-thiadiazole

HRID 1594424Notes

Reaction equation

HRID 1594424 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]1[S:12][N:11]=[C:10](SC)[N:9]=1.Cl[C:16]1C=C(C=CC=1)C(OO)=O.[S:26]([O-:29])(O)=[O:27].[Na+]>C(Cl)(Cl)Cl>[CH3:16][S:26]([C:10]1[N:9]=[C:8]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])[S:12][N:11]=1)(=[O:29])=[O:27]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 586104425-(2-Methylcyclohexyl)-3-methylthio-1,2,4-thiadiazole

Product 1

HCID 690272813-Methylsulfonyl-5-(2-methylcyclohexyl)-1,2,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

500 mg of 5-(2-methylcyclohexyl)-3-methylthio-1,2,4-thiadiazole was dissolved in 6.5 ml of chloroform, 1.62 g of 3-chloroperoxybenzoic acid (content>65%) was added thereto taking for 20 minutes, and the reaction mixture was stirred for 30 minutes under ice-cooling and for 1.5 hours under room temperature. Then, the reaction mixture was added to saturated sodium hydrogensulfite aqueous solution, and separated. The organic layer was washed with sodium hydrogencarbonate aqueous solution, dried over anhydrous sodium sulfate, concentrated to give 466 mg of 3-methylsulfonyl-5-(2-methylcyclohexyl)-1,2,4-thiadiazole.

Workup

  1. customseparated
  2. washThe organic layer was washed with sodium hydrogencarbonate aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d6bce006443c4f34916cebb22f0cf0b6
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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