Acetic Acid → HCID 178495390, compound

HRID 394826Notes

Reaction equation

HRID 394826 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13].C([O-])([O-])=[O:26].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].O.C(O)(=O)C>CO.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O>[CH3:1][C:2]1[C:3]([CH2:14][S+:15]([O-:26])[C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 159762Sodium percarbonateHCID 9949996Rabeprazole-thioether

Product 1

HCID 178495390HCID 178495390, compoundYield 200.8%

Reagents, catalysts & solvents 2

HCID 61578Diammonium molybdateCatalystHCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

2.3 g of 2-[[[3-methyl-4-(3-methoxypropoxy)-2-pyridinyl]methyl]thio]-1H-benzimidazol were dissolved in 11.5 ml of methanol and 90 mg of ammonium molybdate were added. The solution was cooled to 5° C. and 0.87 g of sodium percarbonate were added, then kept stirred at this temperature for 6 h. After the reaction finished 22 ml of water were added, then heating to 20° C. and adjusting the pH of the mixture to 7.5 with acetic acid. The mixture is extracted with 50 ml of dichloromethane and the organic phase was separated, which was then washed with 100 ml of water. The solvent was evaporated at a reduced pressure. 2.0 g of rabeprazol were obtained (yield: 81%).

Workup

  1. additionwere added
  2. temperatureheating to 20° C.
  3. extractionThe mixture is extracted with 50 ml of dichloromethane
  4. customthe organic phase was separated
  5. washwhich was then washed with 100 ml of water
  6. customThe solvent was evaporated at a reduced pressure

Sources & evidence

ORD record
ord-829b935ad71c4a469b1fe5253629418b
Source dataset
uspto-grants-2003_08
Patent number
US06603009B2

Reaction notes

Loading…