Sodium Hydroxide → 2-methyl-6-[[(5-methyl-2-pyridyl)methyl]-thio]-5H-1,3-dioxolo(4,5-f)benzimidazole

HRID 1903149Notes

Reaction equation

HRID 1903149 reaction equation
[CH3:1][CH:2]1[O:14][C:5]2=[CH:6][C:7]3[NH:11][C:10]([SH:12])=[N:9][C:8]=3[CH:13]=[C:4]2[O:3]1.[OH-].[Na+].Cl.[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25]Cl)=[N:23][CH:24]=1>O>[CH3:1][CH:2]1[O:3][C:4]2=[CH:13][C:8]3[NH:9][C:10]([S:12][CH2:25][C:22]4[CH:21]=[CH:20][C:19]([CH3:18])=[CH:24][N:23]=4)=[N:11][C:7]=3[CH:6]=[C:5]2[O:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 233137952-(Chloromethyl)-5-methylpyridine hydrochlorideHCID 178434812HCID 178434812, compound

Product 1

HCID 133437922-methyl-6-[[(5-methyl-2-pyridyl)methyl]-thio]-5H-1,3-dioxolo(4,5-f)benzimidazoleYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3.9 g of 2-methyl-5H-1,3-dioxolo-(4,5-f)benzimidazole-6-thiol, suspended in 60 ml of alcohol, were added dropwise while stirring 1.57 g of sodium hydroxide in 30 ml of water and, after 30 minutes, there were added 3.44 g of 5-methyl-2-chloromethylpyridine hydrochloride. The mixture was left to boil at reflux overnight, then evaporated and the residue was taken up in 500 ml of ethyl acetate. This was washed with 100 ml of sodium hydroxide, three times with 100 ml of water, dried over sodium sulfate and evaporated in vacuo. The crude product was recrystallized from ethyl acetate/petroleum ether (low boiling) and there were obtained 4.8 g (81.7% of theory) of 2-methyl-6-[[(5-methyl-2-pyridyl)methyl]-thio]-5H-1,3-dioxolo(4,5-f)benzimidazole of melting point 147°-148° C.

Workup

  1. additionwere added dropwise
  2. waitThe mixture was left
  3. temperatureat reflux overnight
  4. customevaporated
  5. washThis was washed with 100 ml of sodium hydroxide, three times with 100 ml of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe crude product was recrystallized from ethyl acetate/petroleum ether (low boiling)

Sources & evidence

ORD record
ord-b9280360f1184a5282cb6c939fc13d43
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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