Thionyl Chloride → HCID 24988167, compound

HRID 1623607Notes

Reaction equation

HRID 1623607 reaction equation
C(O[CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:9]=[CH:8][N:7]=1)(=O)C.S(Cl)(Cl)=O.[SH:22][C:23]1[NH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=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:22][C:23]2[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[N:24]=2)[C:11]=1[CH3:12])[CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 10942334Sodium MethoxideHCID 68469816HCID 68469816, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 24988167HCID 24988167, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

8.3 g of 2-acetoxymethyl-3-methyl-4-butoxy-pyridine was dissolved in chloroform, and 21.6 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 6.1 g (1 eq.) of 2-mercaptobenzimidazole, 230 mL of a 28% sodium methoxide solution, and 120 mL of methanol, and the mixture was heated to reflux for one hour. Methanol was distilled off, ice was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate. Subsequently, the ethyl acetate solution was concentrated to dryness, and the resulting residue was purified by silica gel column chromatography, and then was concentrated to dryness, to obtain 12.2 g of yellow crystals. 12.2 g of the crystals were recrystallized from ethyl acetate/1-hexane, to obtain 4.2 g of colorless crystals. Total yield 10.8% (purity by HPLC: 97.0%).

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 was added to the residue
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  11. concentrationSubsequently, the ethyl acetate solution was concentrated to dryness
  12. customthe resulting residue was purified by silica gel column chromatography
  13. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-6234bc96cd23427b8bd5fc0bbc4f7add
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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