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

HRID 845521Notes

Reaction equation

HRID 845521 reaction equation
[O:1]1[C:13]2[C:4](=[CH:5][C:6]3[NH:10][C:9]([SH:11])=[N:8][C:7]=3[CH:12]=2)[O:3][CH2:2]1.[Cl-].Cl[CH2:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[CH:19][NH+:18]=1.[OH-].[Na+]>C(O)C.O>[CH3:24][O:23][C:21]1[C:20]([O:25][CH3:26])=[CH:19][N:18]=[C:17]([CH2:16][S:11][C:9]2[NH:10][C:6]3[CH:5]=[C:4]4[O:3][CH2:2][O:1][C:13]4=[CH:12][C:7]=3[N:8]=2)[CH:22]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 201313622-Chloromethyl-4,5-dimethoxypyridinium chlorideHCID 178527753HCID 178527753, compound

Product 1

HCID 201313026-[(4,5-Dimethoxy-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A brownish solid is obtained by the procedure described in Example 13 by reaction of 0.85 g of 5H-[1,3]-dioxolo[4,5-f]-benzimidazole-6-thiol with 0.98 g of 2-chloromethyl-4,5-dimethoxypyridinium chloride in 10 ml of ethanol and 10 ml of water, with the addition of 8.5 ml of 1N sodium hydroxide solution, after a reaction time of 20 hours and after concentration, by removing the solvent in vacuo, to a volume of 10 ml. The crude product is dissolved in 30 ml of methylene chloride, the solution is clarified with fuller's earth (for example, Tonsil®), and concentrated. The residue is crystallized by addition of diisopropyl ether and the now pale yellow solid is boiled up in 5 ml of methanol. 0.90 g (60% of theory) of the title compound is obtained as a colorless solid of m.p. 198°-200° C.

Workup

  1. customA brownish solid is obtained by the procedure
  2. concentrationafter a reaction time of 20 hours and after concentration
  3. customby removing the solvent in vacuo
  4. dissolutionThe crude product is dissolved in 30 ml of methylene chloride
  5. concentrationconcentrated
  6. customThe residue is crystallized by addition of diisopropyl ether

Sources & evidence

ORD record
ord-7c401b73e5a3495099bd1247c695ccae
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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