m-Chloroperbenzoic acid → 5-(4-Chlorobutylsulfonyl)imidazo[1,2-a]pyridine

HRID 357140Notes

Reaction equation

HRID 357140 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1)=[O:7].ClC1C=CC=C(C(OO)=[O:25])C=1.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1)(=[O:25])=[O:7]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 189368535-(4-Chlorobutylsulfinyl)imidazo[1,2-a]pyridine

Product 1

HCID 189368655-(4-Chlorobutylsulfonyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.88 g (3.47 mmol) of 5-(4-chlorobutylsulfinyl)imidazo[1,2-a]pyridine in 15 ml of dichloromethane, 0.90 g (5.20 mmol) of m-chloroperbenzoic acid was added at 0° C., followed by stirring at room temperature for 64 hours. 0.6 g (3.47 mmol) of m-chloroperbenzoic acid was further added to the reaction mixture, followed by stirring for 5 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, extracted with dichloromethane and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4) to yield 0.28 g (29.7%, yellow oily substance) of the desired product.

Workup

  1. stirringby stirring for 5 hours
  2. extractionextracted with dichloromethane
  3. customdried
  4. distillationafter which the solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4)

Sources & evidence

ORD record
ord-641ef69fd219490584fc77f98d89622e
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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