Sodium Sulfite → HCID 67260857, compound

HRID 2359038Notes

Reaction equation

HRID 2359038 reaction equation
[CH:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:7]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[N:6]1)([CH2:3][CH3:4])[CH3:2].ClC1C=CC=C(C(OO)=[O:30])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][N+:13]([O-:30])=[CH:14][CH:15]=2)[C:7]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[N:6]1)([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 67260571HCID 67260571, compound

Product 1

HCID 67260857HCID 67260857, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (1 eq, 7.2 mmol) in 23 mL of dichloromethane was added metachloroperbenzoic acid 70% (1.5 eq, 10.9 mmol) in small portion at 0° C. The reaction was then stirred at room temperature overnight. Sodium sulfite (1.5 eq, 10.9 mmol) was then added and the organic layer was then washed with a 2M solution of potassium carbonate, dried over MgSO4, filtered and concentrated to afford 2.25 g of 4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine N oxide (83% yield) which was used in the next step without further purification.

Workup

  1. washthe organic layer was then washed with a 2M solution of potassium carbonate
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7a60ad03d44642cb920a7ad362fc47a9
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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