Methanol → 1H-Benzimidazole, 2-[[[4-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethyl-2-pyridinyl]methyl]thio]-

HRID 31731Notes

Reaction equation

HRID 31731 reaction equation
[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[CH:12][C:11]=2[CH3:17])[CH2:4][O:3]1.[SH:19][C:20]1[NH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.[OH-].[Na+].[CH3:31]O>>[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:11]([CH3:17])=[CH:12][N:13]=[C:14]([CH2:31][S:19][C:20]3[NH:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)[C:15]=2[CH3:16])[CH2:4][O:3]1

Participants

5

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 866099724-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 248807801H-Benzimidazole, 2-[[[4-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethyl-2-pyridinyl]methyl]thio]-Yield 84.9%

Procedure

To a mixture of 2-(chloromethyl)-(4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridine (837 mg, 2.79 mmol), 2-mercaptobenzimidazole (419 mg, 2.79 mmol) and sodium hydroxide (223 mg, 5.58 mmol), methanol (20 ml) was added and the mixture was stirred at room temperature for 12 hours and 55 minutes. The reaction mixture was concentrated under reduced pressure. Toluene and a 0.1N aqueous sodium hydroxide solution were added to the residue and insoluble substance was removed by filtration, and then, the organic layer was taken out. The aqueous layer was extracted again with toluene. The organic layers were combined and washed with a saturated saline solution, dried over sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure. The residue was dissolved in n-heptane/ethyl acetate (1/1) and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1) to obtain the title compound (980 mg, 84.9%) as a white foam.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionToluene and a 0.1N aqueous sodium hydroxide solution were added to the residue and insoluble substance
  4. customwas removed by filtration
  5. extractionThe aqueous layer was extracted again with toluene
  6. washwashed with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltrated
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. dissolutionThe residue was dissolved in n-heptane/ethyl acetate (1/1)
  11. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1→0/1)

Sources & evidence

ORD record
ord-dbec951eafcb4b7db903accecd071cd9
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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