Sodium Hydroxide → 4,6-dimethyl-5-methoxy-2-[[(3,4-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 2248437Notes

Reaction equation

HRID 2248437 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([S:22][CH2:23][C:24]3[C:29]([CH3:30])=[C:28]([CH3:31])[CH:27]=[CH:26][N:25]=3)[NH:18][C:17]=2[CH:16]=[C:15]([CH3:32])[C:14]=1[O:33][CH3:34].[OH-].[Na+]>C(Cl)Cl.O>[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([S:22]([CH2:23][C:24]3[C:29]([CH3:30])=[C:28]([CH3:31])[CH:27]=[CH:26][N:25]=3)=[O:9])[NH:18][C:17]=2[CH:16]=[C:15]([CH3:32])[C:14]=1[O:33][CH3:34]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 19996498HCID 19996498, compound

Product 1

HCID 199964964,6-dimethyl-5-methoxy-2-[[(3,4-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazoleYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

m-Chloroperbenzoic acid, 91% (0.53 g, 0.0028 mol) dissolved in CH2Cl2 (25 ml) and cooled to -10° C. was added under stirring to 4,6-dimethyl-5-methoxy-2-[[(3,4-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole (0.91 g, 0.0028 mol) dissolved in CH2CI2 (50 ml) maintaining the temperature at -5° C. Stirring was continued at -5° C. for 5 min and then NaOH (0.34 g, 0.0085 mol) dissolved in water (25 ml) was added under vigorous stirring. The two phases were separated and the aqueous phase was washed with CH2Cl2 (10 ml). More CH2Cl2 (50 ml) was added to the aqueous phase, the pH was adjusted to 9.5 by adding 2M HCl and after stirring the phases were separated. The organic phase was dried (Na2SO4), filtered and the solvent was evaporated off giving an oil which was crystallized from CH3CN (15 ml) yielding the desired product (0.3 g, 32%), m.p. 161° C.

Workup

  1. additionwas added
  2. dissolutiondissolved in CH2CI2 (50 ml)
  3. temperaturemaintaining the temperature at -5° C
  4. additionwas added under vigorous stirring
  5. customThe two phases were separated
  6. washthe aqueous phase was washed with CH2Cl2 (10 ml)
  7. additionMore CH2Cl2 (50 ml) was added to the aqueous phase
  8. additionby adding 2M HCl
  9. stirringafter stirring the phases
  10. customwere separated
  11. dry with materialThe organic phase was dried (Na2SO4)
  12. filtrationfiltered
  13. customthe solvent was evaporated off
  14. customgiving an oil which
  15. customwas crystallized from CH3CN (15 ml)

Sources & evidence

ORD record
ord-4f4043cd57dd402d9b6649368302f676
Source dataset
uspto-grants-1991_08
Patent number
US05039806

Reaction notes

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