Sodium Methoxide → HCID 68466120, compound

HRID 1623614Notes

Reaction equation

HRID 1623614 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:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([CH2:30]Cl)[C:25]=1[CH3:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CO.C(OCC)(=O)C>[CH2:14]([O:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([CH2:30][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:25]=1[CH3:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 68466606HCID 68466606, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 68466120HCID 68466120, compoundYield 108.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a liquid prepared by dissolving with stirring 5.7 g (0.038 mol, 0.9 eq.) of 2-mercaptobenzimidazole and 9.7 g (0.0504 mol, 1.2 eq.) of a 28% sodium methoxide solution in 120 mL of methanol, a liquid containing 12.0 g of 4-nonyloxy-2-chloromethyl-3-methylpyridine dissolved in 60 mL of methanol was added at 29° C. Subsequently, the mixture was heated to reflux for 0.5 hours and cooled, and then methanol was solid dried under reduced pressure. A brown oily residue resulting therefrom was dissolved in 240 mL of ethyl acetate, and then the organic layer was washed with 120 mL of water. 36 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 16.4 g of pale green brown crystals. The pale green brown crystals were recrystallized from ethyl acetate (10 vol.), to obtain 5.5 g of pale brown crystals (HPLC: 98.8 Area %, yield 32.9%).

Workup

  1. customTo a liquid prepared
  2. dissolutionby dissolving
  3. additionwas added at 29° C
  4. temperatureSubsequently, the mixture was heated
  5. temperatureto reflux for 0.5 hours
  6. temperaturecooled
  7. customdried under reduced pressure
  8. customA brown oily residue resulting
  9. washthe organic layer was washed with 120 mL of water
  10. addition36 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-767925279e5c42d1bde467b2e3c16853
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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