Hydrochloric Acid → HCID 178488125, compound

HRID 1700823Notes

Reaction equation

HRID 1700823 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]2[NH:7][C:8]([S:10][CH2:11][C:12]3[C:17]([CH3:18])=[C:16](Cl)[C:15]([CH3:20])=[CH:14][N:13]=3)=[N:9][C:5]=2[CH:4]=1.[CH3:23][OH:24].C[O-].[Na+].Cl>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]2[NH:7][C:8]([S:10][CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:24][CH3:23])[C:15]([CH3:20])=[CH:14][N:13]=3)=[N:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 1784881224-Desmethoxy-4-chloro Omeprazole Sulfide

Product 1

HCID 178488125HCID 178488125, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

First, 277 mg (0.92 mmol) of 5-methoxy-2-{[(4-chloro-3,5-dimethyl-2-pyridyl)methyl]thio}-1H-benzimidazole obtained in Example 21 and 1.00 g (5.20 mmol) of methanol 28% solution of sodium methoxide were introduced to a 3-necked flask (30 ml volume) equipped with a thermometer, a magnetic stirrer and a condenser tube, and the mixture was agitated for 10 hours while being slowly refluxed. Then the mixture was neutralized with dilute hydrochloric acid. Ethyl acetate (10 ml) was added thereto and an organic layer was separated, and an aqueous layer was extracted twice with 10 ml of ethyl acetate. The extracts and the above mentioned organic layer were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 232 mg of 5-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio}-1H-benzimidazole (yield of 85%) with revealing the properties.

Workup

  1. customequipped with a thermometer, a magnetic stirrer and a condenser tube
  2. temperaturewhile being slowly refluxed
  3. customan organic layer was separated
  4. extractionan aqueous layer was extracted twice with 10 ml of ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b5b552b356c4355b7ec698af979dc80
Source dataset
uspto-grants-2002_02
Patent number
US06350876B2

Reaction notes

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