Sodium Hydroxide → Rabeprazole-thioether

HRID 226228Notes

Reaction equation

HRID 226228 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-benzimidazolethiol (15.0 g (100 mmol)), and sodium hydroxide (13.4 g (335 mmol)) were added together, and reaction was carried out for approximately 2 hours at 50° C. After it had been confirmed by TLC that the starting material had disappeared, vacuum concentration was carried out, and toluene (300 ml) and water (168 ml) were then added. After stirring and then leaving to stand, the aqueous layer was separated off. The organic layer was washed with a 10% sodium hydroxide aqueous solution (50 ml), and twice with water (50 ml), and then vacuum concentration was carried out, thus obtaining crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (34.8 g) (HPLC purity 98.7%, yield 101%).

Workup

  1. customreaction
  2. concentrationvacuum concentration
  3. additiontoluene (300 ml) and water (168 ml) were then added
  4. customleaving
  5. customthe aqueous layer was separated off
  6. washThe organic layer was washed with a 10% sodium hydroxide aqueous solution (50 ml)
  7. concentrationtwice with water (50 ml), and then vacuum concentration

Sources & evidence

ORD record
ord-7dedd0b742fe4e26a60946ce4176714d
Source dataset
uspto-grants-2009_07
Patent number
US07557217B2

Reaction notes

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