Sodium Hydroxide → HCID 66702670, compound

HRID 424646Notes

Reaction equation

HRID 424646 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[S:15][N:14]=1.[OH-].[Na+]>C(O)(=O)C.ClCCl.O>[CH3:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[S:15][N+:14]=1[O-:9]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 124969753-Methyl[1,2]thiazolo[5,4-b]pyridine

Product 1

HCID 66702670HCID 66702670, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of m-chloroperbenzoic acid (160 mmol) in acetic acid (200 mL) was added dropwise to a solution of 3-methylisothiazolo[5,4-b]pyridine (107 mmol) in dichloromethane (200 mL). The reaction mixture was maintained for 6 h at 25° C. The reaction mixture was diluted with water (100 mL), the pH was adjusted to 8 with 10% sodium hydroxide, and the layers were separated. The aqueous layer was extracted with ethyl acetate (10×100 mL) and the combined organic layers were dried (magnesium sulfate) and concentrated to provide 3-methylisothiazolo[5,4-b]pyridine-N-oxide in 62% yield as a yellow solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate (10×100 mL)
  3. dry with materialthe combined organic layers were dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8722a88d67c4afeb471c3007d47c539
Source dataset
uspto-grants-2012_01
Patent number
US08106066B2

Reaction notes

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