Hydrogen Peroxide → HCID 178488147, compound

HRID 1067035Notes

Reaction equation

HRID 1067035 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[NH:7][C:8]([S:10][CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[C:15]([CH3:21])=[CH:14][N:13]=3)=[N:9][C:5]=2[CH:4]=1.C1(=O)OC(=[O:28])C2=CC=CC=C12.C(=O)([O-])[O-].[Na+].[Na+].OO>ClCCl.O>[CH3:21][C:15]1[CH:14]=[N:13][C:12]([CH2:11][S+:10]([O-:28])[C:8]2[NH:7][C:6]3[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:9]=2)=[C:17]([CH3:18])[C:16]=1[O:19][CH3:20]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6811Phthalic AnhydrideHCID 10340Sodium CarbonateHCID 178488125HCID 178488125, compound

Product 1

HCID 178488147HCID 178488147, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridinyl)methylthio]-1H-benzimidazole (11) (32.9 gm, 0.1 mole) in dichloromethane (200 ml) was added phthalic anhydride (20 gm, 0.135 mole) and cooled in an ice salt bath. This was followed by addition of sodium carbonate (18 gm, 0.17 mole) and water (20 ml). Hydrogen peroxide (12 ml, 45%, 0.16 mm mole) was added dropwise at −5 to 0° C. and the reaction mixture was stirred at the same temperature. When the reaction was complete as indicated by TLC, water (200 ml) was added, cooling bath was removed and the reaction mixture was stirred for 10 mins. The organic layer was separated and washed with 5% sodium carbonate solution. The separated dichloromethane solution was charcolised and filtered through celite. The filtrate was concentrated to 100 ml and ethyl acetate 100 ml was added thereto. The separated solid was filtered, washed with ethyl acetate and dried in vacuum oven to yield 28.20 gm of Omeprazole. Yield 82.4% of theoretical. Melting Point was 158-160° C. (dec.)

Workup

  1. temperaturecooled in an ice salt bath
  2. additionwas added
  3. temperaturecooling bath
  4. customwas removed
  5. stirringthe reaction mixture was stirred for 10 mins
  6. customThe organic layer was separated
  7. washwashed with 5% sodium carbonate solution
  8. filtrationfiltered through celite
  9. concentrationThe filtrate was concentrated to 100 ml and ethyl acetate 100 ml
  10. additionwas added
  11. filtrationThe separated solid was filtered
  12. washwashed with ethyl acetate
  13. customdried in vacuum oven

Sources & evidence

ORD record
ord-cc5eb2e9b90b45f2b617d83bc4337886
Source dataset
uspto-grants-2001_06
Patent number
US06245913B1

Reaction notes

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