m-Chloroperbenzoic acid → 2-(2,6-Dimethylphenyl)sulfinyl-5-methyl-1,3,4-oxadiazole

HRID 1379090Notes

Reaction equation

HRID 1379090 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9][C:10]1[O:11][C:12]([CH3:15])=[N:13][N:14]=1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([C:10]1[O:11][C:12]([CH3:15])=[N:13][N:14]=1)=[O:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 229096302-(2,6-Dimethylphenyl)thio-5-methyl-1,3,4-oxadiazole

Product 1

HCID 229096442-(2,6-Dimethylphenyl)sulfinyl-5-methyl-1,3,4-oxadiazoleYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 2-(2,6-dimethylphenyl)thio-5-methyl-1,3,4-oxadiazole (0.350 g, 0.0016 mol) in CH2Cl2 (10 ml) was added dropwise m-CPBA (0.530 g, 0.002 mol, 65% pure) in CH2Cl2 (5 ml). The ice bath was removed and the reaction mixture was stirred at rt for 2 h and treated with sat. aq. Na2S2O3 (2.5 ml) solution and sat. aq. Na2CO3 (10 ml). The organic layer was separated and then the aqueous layer was extracted with CH2Cl2 (2×25 ml), dried (MgSO4) and the solvent evaporated in vacuo. Chromatography on silica gel using ethyl acetate/hexanes (1/1) as the eluant gave 2-(2,6-dimethylphenyl)sulfinyl-5-methyl-1,3,4-oxadiazole (78) (0.125 g, 23%) as a white solid; mp 79°-80° C.

Workup

  1. customThe ice bath was removed
  2. additiontreated with sat. aq. Na2S2O3 (2.5 ml) solution and sat. aq. Na2CO3 (10 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×25 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-0988530654dc47f4bdb1cc298d3775ac
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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