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Sodium Hydroxide → HCID 178488147, compound

HRID 275013
Notes
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Reaction equation

HRID 275013 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S:12][C:13]2[NH:17][C:16]3[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[N:4][CH:3]=1.C(=O)(O)[O-:25].[K+].C1C=C(C([O-])=O)C(C(O[O-])=O)=CC=1.[Mg+2].S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>O.CO.C(O)C.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:25])[C:13]2[NH:14][C:15]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:16]=3[N:17]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 155794Omeprazole sulfideHCID 516893Potassium BicarbonateHCID 10130449Monoperoxyphthalic Acid Magnesium Salt2×

Product 1

HCID 178488147HCID 178488147, compound
Yield 81%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent4×HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of pyrmetazole (0.112 mole) and potassium bicarbonate (0.145 mole) in 100 mL of water and approximately 250 mL of a 4:1; toluene: ethanol mixture was cooled to -5° to -9° C. with stirring. A solution of MMPP (0.67 mol) in 170 mL of water was added dropwise over a 2 hour period. After the MMPP solution was completely added a solution of sodium sulfite (2.2g) in 10 mL of water was added and the mixture was stirred for 15 minutes. The reaction mixture temperature was allowed to warm to 0° C. during this period. The slurry was then diluted with 200 mL of water and 50 mL of methanol and the pH of the slurry was adjusted to 9.1 by addition of 50% aqueous sodium hydroxide. The slurry was aged at 0° to 5° C. for 1 hour and then was filtered. The solid was washed with 50 mL of water and 40 mL cold methanol. Drying of the solid provided 31.3 g of crude omeprazole (81% yield).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 15 minutes
  3. filtrationwas filtered
  4. washThe solid was washed with 50 mL of water and 40 mL cold methanol
  5. customDrying of the solid

Sources & evidence

ORD record
ord-b6a15d6f76b6457697cb9df2e62aa10d
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05391752

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes