m-Chloroperbenzoic acid → 2-Methyl-thiazolo[4,5-c]pyridine 5-oxide

HRID 1443104Notes

Reaction equation

HRID 1443104 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.ClC1C=C(C=CC=1)C(OO)=[O:16]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N+:7]([O-:16])=[CH:6][C:5]=2[N:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6407212-Methyl-[1,3]thiazolo[4,5-c]pyridine

Product 1

HCID 685381222-Methyl-thiazolo[4,5-c]pyridine 5-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Methyl-thiazolo[4,5-c]pyridine (2.3 g, 15.3 mmol) was dissolved in 150 ml chloroform and 3-chloroperoxybenzoic acid (4.15 g, 16.8 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 hour and then evaporated. The residue was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient). The desired product was obtained as a white solid (2.1 g, 83%), MS: m/e=167.2 (M+H+).

Workup

  1. customevaporated
  2. customThe residue was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient)

Sources & evidence

ORD record
ord-b0d2d92962c54d748556450ddbe8f599
Source dataset
uspto-grants-2010_02
Patent number
US07659401B2

Reaction notes

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