Potassium peroxymonosulphate → 6-chloro-2-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

HRID 929184Notes

Reaction equation

HRID 929184 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9](SC)=[N:10][C:4]=2[CH:3]=1.[S:13]([O-:18])(O[O-])(=O)=[O:14].[K+].[K+].[CH3:21]C#N.O>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9]([S:13]([CH3:21])(=[O:18])=[O:14])=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 10313463Potassium peroxymonosulphateHCID 18373917Acetonitrile--water (1/1)HCID 900421086-Chloro-2-(methylthio)-3H-imidazo[4,5-c]pyridine

Product 1

HCID 900420736-chloro-2-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine

Procedure

To a stirring solution of 6-chloro-2-(methylthio)-3H-imidazo[4,5-c]pyridine (954.0 mg, 4.78 mmol) in 50% CH3CN/water (61.4 mL) was added potassium peroxymonosulfate (oxone, 6.46 g, 10.51 mmol). The reaction was stirred under N2 at RT for 15 h, then filtered and the filtrate added to a stirring mixture of EtOAc (1.27 L)/water (0.70 L). The aqueous layer was separated and back-extracted with EtOAc (0.25 L). The combined organic layers were evaporated under reduced pressure to afford the title compound. LC-MS: calculated for C7H6ClN3O2S 230.99 observed m/e: 231.98 (M+H)+ (Rt 1.72/2.0 min)

Workup

  1. filtrationfiltered
  2. additionthe filtrate added to a stirring mixture of EtOAc (1.27 L)/water (0.70 L)
  3. customThe aqueous layer was separated
  4. extractionback-extracted with EtOAc (0.25 L)
  5. customThe combined organic layers were evaporated under reduced pressure

Sources & evidence

ORD record
ord-08fa05f92f9845bb87f9b0b0cc83139a
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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