Sodium Methoxide → HCID 24988168, compound

HRID 1623604Notes

Reaction equation

HRID 1623604 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:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH2:27]Cl)[C:22]=1[CH3:29])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CO.C(OCC)(=O)C>[CH2:14]([O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH2:27][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:22]=1[CH3:29])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 68467052HCID 68467052, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 24988168HCID 24988168, compoundYield 25.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a liquid prepared by dissolving with stirring 7.8 g (0.052 mol, 0.95 eq.) of 2-mercaptobenzimidazole and 61.5 g (0.319 mol, 5.8 eq.) of a 28% sodium methoxide solution in 360 mL of methanol, a liquid prepared by dissolving the whole amount of 4-hexyloxy-2-chloromethyl-3-methylpyridine in 180 mL of methanol was added at 30° C. Subsequently, the mixture was heated to reflux for 30 minutes and cooled, and then methanol was solid dried under reduced pressure. A yellow brown oily residue resulting therefrom was dissolved in 200 mL of ethyl acetate, and then the organic layer was washed with 80 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 15.2 g of an orange-colored oily matter. The product was recrystallized from ethyl acetate (5 vol.), to obtain 5.0 g of colorless crystals (HPLC: 99.1 Area %, yield 25.5%).

Workup

  1. customTo a liquid prepared
  2. dissolutionby dissolving
  3. customa liquid prepared
  4. additionwas added at 30° C
  5. temperatureSubsequently, the mixture was heated
  6. temperatureto reflux for 30 minutes
  7. temperaturecooled
  8. customdried under reduced pressure
  9. customA yellow brown oily residue resulting
  10. washthe organic layer was washed with 80 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 15.2 g of an orange-colored oily matter
  16. customThe product was recrystallized from ethyl acetate (5 vol.)

Sources & evidence

ORD record
ord-194ade9b048f4a2f876bec6cc68f4ed5
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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