Thionyl Chloride → 2-[[(4-Methoxy-3-methyl-2-pyridinyl)methyl]thio]-1H-benzimidazole

HRID 1623610Notes

Reaction equation

HRID 1623610 reaction equation
C(O[CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][N:7]=1)(=O)C.S(Cl)(Cl)=O.[SH:19][C:20]1[NH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C[O-].[Na+]>C(Cl)(Cl)Cl.CO>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][S:19][C:20]2[NH:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[N:21]=2)[C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 105840092-acetoxymethyl-3-methyl-4-methoxy-pyridineHCID 10942334Sodium MethoxideHCID 178527775HCID 178527775, compound

Product 1

HCID 108030672-[[(4-Methoxy-3-methyl-2-pyridinyl)methyl]thio]-1H-benzimidazoleYield 85.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

5.7 g of 2-acetoxymethyl-3-methyl-4-methoxy-pyridine was dissolved in chloroform, and 18 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 5.3 g (1 eq.) of 2-mercaptobenzimidazole, 45 mL of a 28% sodium methoxide solution, and 100 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 then were washed by suspending in water, to obtain 7.1 g of colorless crystals. Total yield 20.9% (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. washwere washed

Sources & evidence

ORD record
ord-ab0b7b39dca34516bfeefc30a6a37041
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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