Sodium Hydroxide → Rabeprazole-thioether

HRID 1171874Notes

Reaction equation

HRID 1171874 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+]>O>[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 Hydroxide2×HCID 110316672-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 9949996Rabeprazole-thioether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To this 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridin solution was added 2-benzimidazole thiol (8.71 g (58.0 mmol)) at room temperature. A 25% aqueous sodium hydroxide solution (40.6 g) was added gradually as the temperature (internal temperature) was gradually raised to 65° C. The reaction mixture was stirred for about an hour and a half at 65° C. (internal temperature). Water (60.0 ml) was added to the reaction mixture at 65° C., after which 25% aqueous sodium hydroxide solution (0.2 g) was added and stirred. This reaction mixture was allowed to stand, and the water layer was separated. The organic layer was washed with water (20.0 ml) twice, and toluene (79.6 ml) and methanol (21.5 ml) were added to the organic layer to obtain a 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole solution.

Workup

  1. customat 65° C.
  2. stirringstirred
  3. customthe water layer was separated
  4. washThe organic layer was washed with water (20.0 ml) twice
  5. additiontoluene (79.6 ml) and methanol (21.5 ml) were added to the organic layer

Sources & evidence

ORD record
ord-00f83658a0a44967b6500c809a55e1a8
Source dataset
uspto-grants-2010_11
Patent number
US07829718B2

Reaction notes

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