Sodium Methoxide → HCID 24988169, compound

HRID 1623606Notes

Reaction equation

HRID 1623606 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C[O-].[Na+].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([CH2:28]Cl)[C:23]=1[CH3:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CO.C(OCC)(=O)C>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([CH2:28][S:1][C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)[C:23]=1[CH3:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 68468291HCID 68468291, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 24988169HCID 24988169, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a liquid prepared by dissolving with stirring 8.7 g (0.058 mol, 0.95 eq.) of 2-mercaptobenzimidazole and 68.2 g (0.354 mol, 5.8 eq.) of a 28% sodium methoxide solution in 400 mL of methanol, a liquid prepared by dissolving the whole amount of 4-heptyloxy-2-chloromethyl-3-methylpyridine in 210 mL of methanol was added at 28° C. Subsequently, the mixture was heated to reflux for one hour and cooled, and then methanol was solid dried under reduced pressure. A yellow brown oily residue resulting therefrom was dissolved in 250 mL of ethyl acetate, and then the organic layer was washed with 100 mL of water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated to dryness. The resulting residue was purified by silica gel column chromatography, and then was concentrated to dryness, to obtain 17.8 g of an orange-colored oily matter. The orange-colored oily matter was recrystallized from ethyl acetate (7 vol.), to obtain 8.7 g of colorless crystals (HPLC: 99.0 Area %, yield 38.7%).

Workup

  1. customTo a liquid prepared
  2. dissolutionby dissolving
  3. customa liquid prepared
  4. additionwas added at 28° C
  5. temperatureSubsequently, the mixture was heated
  6. temperatureto reflux for one hour
  7. temperaturecooled
  8. customdried under reduced pressure
  9. customA yellow brown oily residue resulting
  10. washthe organic layer was washed with 100 mL of water
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated to dryness
  13. customThe resulting residue was purified by silica gel column chromatography
  14. concentrationwas concentrated to dryness
  15. customto obtain 17.8 g of an orange-colored oily matter
  16. customThe orange-colored oily matter was recrystallized from ethyl acetate (7 vol.)

Sources & evidence

ORD record
ord-6437fe03dcba4d7e9b7ae6255bddd2d4
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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