Thionyl Chloride → HCID 14097116, compound

HRID 1623612Notes

Reaction equation

HRID 1623612 reaction equation
C(O[CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:8][N:7]=1)(=O)C.S(Cl)(Cl)=O.[SH:21][C:22]1[NH:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=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:21][C:22]2[NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]=2)[C:11]=1[CH3:12])[CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 10942334Sodium MethoxideHCID 684689472-Acetoxymethyl-3-methyl-4-propoxy-pyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 14097116HCID 14097116, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

11.0 g of 2-acetoxymethyl-3-methyl-4-propoxy-pyridine was dissolved in chloroform, and 30 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 8.7 g (1 eq.) of 2-mercaptobenzimidazole, 73 mL of a 28% sodium methoxide solution, and 300 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 15.5 g of yellow crystals. The yellow crystals were recrystallized from ethyl acetate, to obtain 6.3 g of colorless crystals. Total yield 17% (purity by HPLC: 98.1%).

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-0f2b1f526a8c472f81bdccb81a7e3df7
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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