HCID 22909633, compound → HCID 9817195, compound

HRID 1379088Notes

Reaction equation

HRID 1379088 reaction equation
CC1OC(SCC2C(C)=C(OC)C(C)=C[N+]=2[O-])=NN=1.[CH3:20][C:21]1[O:25][C:24]([S:26]([CH2:28][C:29]2[C:34]([CH3:35])=[C:33]([O:36][CH3:37])[C:32]([CH3:38])=[CH:31][N+:30]=2[O-])=[O:27])=[N:23][N:22]=1>>[CH3:35][C:34]1[C:29]([CH2:28][S:26]([C:24]2[O:25][C:21]([CH3:20])=[N:22][N:23]=2)=[O:27])=[N:30][CH:31]=[C:32]([CH3:38])[C:33]=1[O:36][CH3:37]

Participants

3

Reactant 2

HCID 22909633HCID 22909633, compoundHCID 22909645HCID 22909645, compound

Product 1

HCID 9817195HCID 9817195, compound

Procedure

The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×50 ml), dried (Mg2SO4) and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using ethyl acetate to CH2Cl2 /MeOH (20/1) to give 2-(3,5-dimethyl-4-methoxy-2-pyridyl)methylsulfinyl-5-methyl-1,3,4-oxadiazole (70) (5.44 g, 19%, mp 114°-115° C.) along with unreacted starting material (3.82 g) and the N-oxidized products 2-(5-methyl-1,3,4-oxadiazol-2-yl)thiomethyl-3,5-dimethyl-4-methoxypyridine-N-oxide and 2-(5-methyl-1,3,4-oxadiazol-2-yl)sulfinylmethyl-3,5-dimethyl-4-methoxypyridine-N-oxide (15.76 g).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×50 ml)
  3. dry with materialdried (Mg2SO4)
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. customto give 2-(3,5-dimethyl-4-methoxy-2-pyridyl)methylsulfinyl-5-methyl-1,3,4-oxadiazole (70) (5.44 g, 19%, mp 114°-115° C.) along

Sources & evidence

ORD record
ord-e84b4f87ca5c44fb989620a65b288bf0
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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