Sodium Methoxide → HCID 68469300, compound

HRID 1623616Notes

Reaction equation

HRID 1623616 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:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([CH2:31]Cl)[C:26]=1[CH3:33])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CO.C(OCC)(=O)C>[CH2:14]([O:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([CH2:31][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:26]=1[CH3:33])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 68468382HCID 68468382, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 68469300HCID 68469300, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a liquid prepared by dissolving with stirring 6.8 g (0.045 mol, 0.9 eq.) of 2-mercaptobenzimidazole and 11.6 g (0.06 mol, 1.2 eq.) of a 28% sodium methoxide solution in 150 mL of methanol, a liquid containing 15.0 g of 4-decyloxy-2-chloromethyl-3-methylpyridine dissolved in 75 mL of methanol was added at 30° C. Subsequently, the mixture was heated to reflux for 0.5 hours and cooled, and then methanol was solid dried under reduced pressure. An orange-colored oily residue resulting therefrom was dissolved in 300 mL of ethyl acetate, and then the organic layer was washed with 150 mL of water. 45 g of silica gel was added with stirring to the organic layer, subsequently the silica gel was removed by filtration, and then the filtrate was concentrated to dryness under reduced pressure, to obtain 18.5 g of pale orange crystals. The pale orange crystals were recrystallized from ethyl acetate (10 vol.), to obtain 9.7 g of pale orange crystals (HPLC: 99.6 Area %, yield 47.1%).

Workup

  1. customTo a liquid prepared
  2. dissolutionby dissolving
  3. additionwas added at 30° C
  4. temperatureSubsequently, the mixture was heated
  5. temperatureto reflux for 0.5 hours
  6. temperaturecooled
  7. customdried under reduced pressure
  8. customAn orange-colored oily residue resulting
  9. washthe organic layer was washed with 150 mL of water
  10. addition45 g of silica gel was added
  11. customsubsequently the silica gel was removed by filtration
  12. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7685335662dd40f1b776f91cf9ffccbd
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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