Sodium Methoxide → HCID 24852840, compound

HRID 1623602Notes

Reaction equation

HRID 1623602 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:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([CH2:26]Cl)[C:21]=1[CH3:28])[CH2:15][CH2:16][CH2:17][CH3:18]>CO.C(OCC)(=O)C>[CH2:14]([O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([CH2:26][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:21]=1[CH3:28])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 68470112HCID 68470112, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 24852840HCID 24852840, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a liquid prepared by dissolving with stirring 7.5 g (0.052 mol, 1.0 eq.) of 2-mercaptobenzimidazole and 61.5 g (0.319 mol, 5.8 eq.) of a 28% sodium methoxide solution in 120 mL of methanol, a liquid prepared by dissolving the whole amount of 4-pentyloxy-2-chloromethyl-3-methylpyridine in 180 mL of methanol was added at 30° 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 6.9 g of amorphous solidified product. The product was recrystallized from an ethyl acetate/1-hexane mixed liquid, to obtain 4.3 g of colorless crystals (HPLC: 98.5 Area %, yield 10.6%).

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 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

Sources & evidence

ORD record
ord-b529063789c34b57bf2f1537c4ac2485
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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