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

HRID 703190Notes

Reaction equation

HRID 703190 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]([CH3:25])=[CH:19][N:18]=1.[OH-].[Na+]>O>[CH3:24][O:23][C:21]1[C:20]([CH3:25])=[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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 221514312-(Chloromethyl)-4-methoxy-5-methylpyridine hydrochlorideHCID 178527753HCID 178527753, compound

Product 1

HCID 221514306-[[(4-methoxy-5-methyl-2-pyridyl)-methyl]thio]-5H-1,3-dioxolo[4,5-f]benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.82 g of 5H-1,3-dioxolo[4,5-f]benzimidazole-6-thiol were suspended in 200 ml of alcohol and the suspension was treated with 6.3 g of 2-chloromethyl-4-methoxy-5-methylpyridine hydrochloride while cooling. 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 methylene chloride/petroleum ether gave 6-[[(4-methoxy-5-methyl-2-pyridyl)-methyl]thio]-5H-1,3-dioxolo[4,5-f]benzimidazole of melting point 191°-193°.

Workup

  1. temperaturewhile cooling
  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 methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-2ddeaf8d2038465ab5bcccab4fe183ce
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

Loading…