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

HRID 979879Notes

Reaction equation

HRID 979879 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[C:22]([CH3:23])=[C:21]([O:24][CH2:25][CH3:26])[C:20]([CH3:27])=[CH:19][N:18]=1.[OH-].[Na+]>C(O)C.O>[CH2:25]([O:24][C:21]1[C:20]([CH3:27])=[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)[C:22]=1[CH3:23])[CH3:26]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 221514582-Chloromethyl-4-ethoxy-3,5-dimethylpyridine hydrochlorideHCID 178527753HCID 178527753, compound

Product 1

HCID 221514556-[[(4-ethoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5H-1,3-dioxolo[4,5-f]benzimidazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5.82 g of 5H-1,3-dioxolo[4,5-f]benzimidazole-6-thiol were suspended in 200 ml of ethanol and the suspension was treated with 7.1 g 2-chloromethyl-4-ethoxy-3,5-dimethylpyridine hydrochloride while cooling with ice. Thereafter, a solution of 2.4 g of sodium hydroxide in 100 ml of water was added dropwise thereto, the mixture was left to boil at reflux overnight and subsequently evaporated to dryness in vacuo. The residue was dissolved in 500 ml of methylene chloride. The solution was washed firstly with 250 ml of 1.5N sodium hydroxide solution and then with 3×300 ml of water, dried over sodium sulfate and evaporated in vacuo. The product was purified on 150 g of silica gel using ethyl acetate/methylene chloride (1:1) as the elution agent. Crystallization from acetonitrile gave 6-[[(4-ethoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5H-1,3-dioxolo[4,5-f]benzimidazole of melting point 184°-185°.

Workup

  1. temperaturewhile cooling with ice
  2. waitthe mixture was left
  3. temperatureat reflux overnight
  4. customsubsequently evaporated to dryness in vacuo
  5. dissolutionThe residue was dissolved in 500 ml of methylene chloride
  6. washThe solution was washed firstly with 250 ml of 1.5N sodium hydroxide solution
  7. dry with materialwith 3×300 ml of water, dried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe product was purified on 150 g of silica gel
  10. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-f92fc5b403e24a3787f83037c4634a3f
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

Loading…