Sodium Thiosulfate → 5-(methylsulfonyl)-2-(5-phenyl-1H-imidazol-1-yl)pyridine

HRID 1523269Notes

Reaction equation

HRID 1523269 reaction equation
Cl[C:2]1C=C(C=CC=1)C(OO)=O.CS[C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:23][N:22]=[CH:21]2)=[N:18][CH:19]=1.[O-:31][S:32]([O-:35])(=S)=O.[Na+].[Na+]>ClCCl>[CH3:2][S:32]([C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:23][N:22]=[CH:21]2)=[N:18][CH:19]=1)(=[O:35])=[O:31]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 866946815-(methylthio)-2-(5-phenyl-1H-imidazol-1-yl)pyridine

Product 1

HCID 680162165-(methylsulfonyl)-2-(5-phenyl-1H-imidazol-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

M-chloroperoxybenzoic acid (230 g) and 5-(methylthio)-2-(5-phenyl-1H-imidazol-1-yl)pyridine (118 g) were dissolved in 3 L dichloromethane, and stirred to react for 2 hours at 0° C. After the reaction was complete, 1000 mL saturated Na2S2O3 solution was added. The mixture was extracted with dichloromethane, the organic phase was washed with saturated NaCl solution, and dried with anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by column chromatography to obtain the target compound (50 g). 1H-NMR (300 MHz, CDCl3): δ 3.14 (3H, s), 6.90 (1H, d), 7.24 (3H, m), 7.39 (3H, m), 8.06 (1H, dd), 8.30 (1H, s), 9.05 (1H, d); LC-MS m/z: 300 [M++1], purity (HPLC)>95%.

Workup

  1. customto react for 2 hours at 0° C
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe organic phase was washed with saturated NaCl solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-bfca93a3f9404c418104b3d983dec2ef
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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