Water → 4-(4-Cyclopropyl-5-methanesulfonyl-4H-[1,2,4]triazol-3-yl)-pyridine

HRID 639783Notes

Reaction equation

HRID 639783 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH:7]1([N:10]2[C:14]([S:15][CH3:16])=[N:13][N:12]=[C:11]2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:9][CH2:8]1.S([O-])(O)=[O:24].[Na+].[OH2:28]>C(O)(=O)C>[CH:7]1([N:10]2[C:14]([S:15]([CH3:16])(=[O:24])=[O:28])=[N:13][N:12]=[C:11]2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 578379714-(4-Cyclopropyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)-pyridine

Product 1

HCID 578379334-(4-Cyclopropyl-5-methanesulfonyl-4H-[1,2,4]triazol-3-yl)-pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of potassium permanganate (525 mg, 3.3 mmol) in water (22.0 mL) was added to a solution of 4-(4-cyclopropyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)-pyridine (514 mg, 2.2 mmol) in acetic acid (11 mL) drop-wise at room temperature. After stirring for 3 hours, sodium hydrogen sulfite was added until the purple color was discharged. The reaction mixture was extracted with chloroform and then the organic layer was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated to afford the titled compound (546.7 mg, 94%, white solid). 1H NMR (CDCl3) δ (ppm): 8.86 (d, 2H), 7.77 (d, 2H), 3.64 (m, 1H), 3.63 (s, 3H), 1.25 (m, 2H), 1.01 (m, 2H).

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2f67ebd4a0424627a6d95ab5900cec17
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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