Sodium Hydroxide → Rabeprazole-thioether

HRID 226227Notes

Reaction equation

HRID 226227 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%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine (53.2 g (200 mmol)), denatured ethanol (320 ml), 2-benzimidazolethiol (30.2 g (201 mmol)), and sodium hydroxide (26.8 g (670 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 ethyl acetate (430 ml) and water (340 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 (110 ml), and twice with water (110 ml), and then vacuum concentration was carried out, thus obtaining crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (69.0 g) (HPLC purity 98.7%, yield 101%).

Workup

  1. customreaction
  2. concentrationvacuum concentration
  3. additionethyl acetate (430 ml) and water (340 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 (110 ml)
  7. concentrationtwice with water (110 ml), and then vacuum concentration

Sources & evidence

ORD record
ord-8cdaa3119709404ca10b23f3c7266449
Source dataset
uspto-grants-2009_07
Patent number
US07557217B2

Reaction notes

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