Thionyl Chloride → HCID 10780508, compound

HRID 1623611Notes

Reaction equation

HRID 1623611 reaction equation
C(O[CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH3:15])[CH:9]=[CH:8][N:7]=1)(=O)C.S(Cl)(Cl)=O.[SH:20][C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C[O-].[Na+]>C(Cl)(Cl)Cl.CO>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][S:20][C:21]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[N:22]=2)[C:11]=1[CH3:12])[CH3:15]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 10750907HCID 10750907, compoundHCID 10942334Sodium MethoxideHCID 178527775HCID 178527775, compound

Product 1

HCID 10780508HCID 10780508, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

10.7 g of 2-acetoxymethyl-3-methyl-4-ethoxy-pyridine was dissolved in chloroform, and 28.2 g (4 eq.) of thionyl chloride was added. The mixture was heated to reflux for one hour and then concentrated, and a residue resulting therefrom was dissolved in methanol. The solution was added in advance to 8.4 g (1 eq.) of 2-mercaptobenzimidazole, 71 mL of a 28% sodium methoxide solution, and 150 mL of methanol, and the mixture was heated to reflux for one hour. Methanol was distilled off, and ice and ethyl acetate were added to the residue, to wash the residue by suspending. Produced crystals were collected by filtration and dissolved in methanol, and the solution was dried over anhydrous magnesium sulfate. Subsequently, the methanol solution was concentrated to dryness, and the resultant was dissolved in chloroform. The chloroform layer was dried over magnesium sulfate and then concentrated to dryness, to obtain an amorphous solid. The solid was washed by suspending in ethyl acetate, to obtain 2.8 g of colorless crystals. Total yield 7.9% (purity by HPLC: 98.2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. concentrationconcentrated
  4. customa residue resulting
  5. temperaturethe mixture was heated
  6. temperatureto reflux for one hour
  7. distillationMethanol was distilled off
  8. additionice and ethyl acetate were added to the residue
  9. washto wash the residue
  10. customProduced crystals
  11. filtrationwere collected by filtration
  12. dissolutiondissolved in methanol
  13. dry with materialthe solution was dried over anhydrous magnesium sulfate
  14. concentrationSubsequently, the methanol solution was concentrated to dryness
  15. dissolutionthe resultant was dissolved in chloroform
  16. dry with materialThe chloroform layer was dried over magnesium sulfate
  17. concentrationconcentrated to dryness
  18. customto obtain an amorphous solid
  19. washThe solid was washed

Sources & evidence

ORD record
ord-91ff63a7adfa4d12bc91c680249b640a
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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