Sodium Hydroxide → Rabeprazole-thioether

HRID 556004Notes

Reaction equation

HRID 556004 reaction equation
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1.[N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18][C:17]=1[SH:25].[OH-].[Na+]>C(O)C>[CH3:15][O:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][S:25][C:17]2[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:16]=2)[C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 110316672-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 9949996Rabeprazole-thioetherYield 101.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine (26.6 g (100 mmol)), denatured ethanol (160 ml), 2-benzimidazole thiol (15.0 g (100 mmol)) and sodium hydroxide (13.4 g (335 mmol)) were added together and reacted for about 2 hours at 50° C. After disappearance of the raw materials had been confirmed by TLC, this solution was concentrated under a reduced pressure, toluene (30 ml) and water (168 ml) were added thereto. After stirring and still standing the water layer was separated. The organic layer was washed with 10% aqueous sodium hydroxide solution (50 ml) and water (2×50 ml) and concentrated under a reduced pressure to obtain crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (34.8 g) (HPLC purity 98.7%, yield 101%).

Workup

  1. customreacted for about 2 hours at 50° C
  2. concentrationthis solution was concentrated under a reduced pressure, toluene (30 ml) and water (168 ml)
  3. additionwere added
  4. customwas separated
  5. washThe organic layer was washed with 10% aqueous sodium hydroxide solution (50 ml) and water (2×50 ml)
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-64de5238492847ee84d5e3bdfed3baf0
Source dataset
uspto-grants-2011_11
Patent number
US08053580B2

Reaction notes

Loading…