Thieno(2,3-c)pyridine → thieno[2,3-c]pyridine-N-oxide

HRID 376313Notes

Reaction equation

HRID 376313 reaction equation
[S:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.ClC1C=CC=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[S:1]1[C:5]2=[CH:6][N+:7]([O-:18])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 9224Thieno(2,3-c)pyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 14666712thieno[2,3-c]pyridine-N-oxideYield 82.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 18 g of thieno[2,3-c]pyridine in 300 ml of chloroform was added 33 g of 3-chloroperbenzoic acid portionwise with ice-cooling over a period of 1 hour, and the mixture was stirred for further 1 hour under the same conditions. The reaction mixture was diluted with 400 ml of chloroform, washed successively with water, a saturated sodium carbonate solution and saturated saline, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure to give 16.6 g of thieno[2,3-c]pyridine-N-oxide as a white powder.

Workup

  1. temperaturecooling over a period of 1 hour
  2. washwashed successively with water
  3. dry with materiala saturated sodium carbonate solution and saturated saline, and dried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6be05489d83a44a893c8911b8dbcab5b
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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