Potassium Carbonate → 5-Fluoro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole

HRID 1709759Notes

Reaction equation

HRID 1709759 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([S:9][CH2:10][C:11]3[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][N:12]=3)[NH:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-:23].[K+].[K+].ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([S:9]([CH2:10][C:11]3[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][N:12]=3)=[O:23])[NH:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19024498HCID 19024498, compound

Product 1

HCID 230365195-Fluoro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2.0 g of 5-fluoro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]benzimidazole dissolved in 100 ml of methylene chloride were treated with 1.2 g of potassium carbonate. 1.6 g of m-chloroperbenzoic acid were added thereto at -30°, the solution was stirred for a further 5 minutes and subsequently poured into a mixture of 30 ml of saturated sodium bicarbonate solution and 30 ml of water. The organic phase was separated, dried over sodium sulfate, treated with 5.0 ml of triethylamine and evaporated in a vacuum. Crystallization of the residue from methylene chloride/petroleum ether (low boiling)/ether gave 5-fluoro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole of melting point 175°.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulfate
  3. additiontreated with 5.0 ml of triethylamine
  4. customevaporated in a vacuum
  5. customCrystallization of the residue from methylene chloride/petroleum ether (low boiling)/ether

Sources & evidence

ORD record
ord-c7a57a8a80ac42dca6ed12c8e8959920
Source dataset
uspto-grants-1990_08
Patent number
US04950677

Reaction notes

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