m-Chloroperbenzoic acid → HCID 23362947, compound

HRID 1081735Notes

Reaction equation

HRID 1081735 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][S:8][C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][S:8]([C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1)=[O:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 233628785-[3-(Acetyloxy)propylthio]imidazo[1,2-a]pyridine

Product 1

HCID 23362947HCID 23362947, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-[3-(acetyloxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 3.99 mmoles) in chloroform (25 ml) was added m-chloroperbenzoic acid (1.47 g, 5.96 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 1.5 hours. The reaction mixture was washed in turn with an aqueous 20% sodium bisulfite solution and an aqueous saturated sodium bicarbonate solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent:hexane/acetone (1:1)] to obtain 0.19 g of 5-[3-(acetyloxy)propylsulfinyl]imidazo[1,2-a]pyridine (Compound 177) (34.6%, yellow oily product) and 0.19 g of 5-(acetyloxy)propylsulfonyl]imidazo[1,2-a]pyridine (Compound 178) (16.5%, yellow oily product).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred under ice-
  3. temperaturecooling for 1.5 hours
  4. washThe reaction mixture was washed in turn with an aqueous 20% sodium bisulfite solution
  5. dry with materialan aqueous saturated sodium bicarbonate solution and dried
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography [eluent:hexane/acetone (1:1)]

Sources & evidence

ORD record
ord-af0ba763a3f1404da5163bbb32adfffc
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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