Potassium Carbonate → Benzimidazole

HRID 1709767Notes

Reaction equation

HRID 1709767 reaction equation
F[C:2]1[C:21](F)=[CH:20][C:5]2[N:6]=[C:7](SCC3C(C)=C(OC)C=CN=3)[NH:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO.O>[N:6]1[C:5]2[CH:20]=[CH:21][CH:2]=[CH:3][C:4]=2[NH:8][CH:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 230365355,6-Difluoro-2-[[(4-methoxy 3-methyl-2-pyridyl)methyl]thio]benzimidazole

Product 1

HCID 5798Benzimidazole

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 13.7 g of 5,6-difluoro-2-[[(4-methoxy 3-methyl-2-pyridyl)methyl]thio]benzimidazole in 800 ml of methylene chloride and 130 ml of methanol was treated with 6.9 g of potassium carbonate. 9.6 g of m-chloroperbenzoic acid were added thereto at -30°, whereupon the solution was stirred for a further 5 minutes and subsequently poured into a mixture of 200 ml of saturated sodium bicarbonate solution and 200 ml of water. The separated organic phase was dried over sodium sulfate, treated with 5.0 ml of triethylamine and evaporated in a vacuum. Crystallization from methylene chloride-methanol-ether yielded 5,6-difluoro-2-[[(4-methoxy-3-methyl-2-pyridyl))methyl]sulfinyl]benzimidazole of melting point 188°-189°.

Workup

  1. dry with materialThe separated organic phase was dried over sodium sulfate
  2. additiontreated with 5.0 ml of triethylamine
  3. customevaporated in a vacuum
  4. customCrystallization from methylene chloride-methanol-ether

Sources & evidence

ORD record
ord-0c7b3786ad1044af94f30e7a08fb1638
Source dataset
uspto-grants-1990_08
Patent number
US04950677

Reaction notes

Loading…