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

HRID 1594419Notes

Reaction equation

HRID 1594419 reaction equation
CS[C:3]1[N:7]=[C:6]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[S:5][N:4]=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:3]1[N:7]=[C:6]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[S:5][N:4]=1)(=[O:29])=[O:27]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 586104393-Methylthio-5-(cyclohexyl)methyl-1,2,4-thiadiazole

Product 1

HCID 690245423-Methylsulfonyl-5-(cyclohexyl)methyl-1,2,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.2 g of 3-methylthio-5-(cyclohexyl)methyl-1,2,4-thiadiazole was dissolved in 20 ml of chloroform, 2.78 g of 3-chloroperoxybenzoic acid (content>65%) was added thereto, and the reaction mixture was stirred for 1 hour under ice-cooling and for 16 hours at 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 1.4 g of 3-methylsulfonyl-5-(cyclohexyl)methyl-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-59a78a59556248c28fc5abf310fb4ea5
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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