Trichloroethylene → HCID 23681230, compound

HRID 1532922Notes

Reaction equation

HRID 1532922 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:24])[C:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=3[N:21]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].[OH-:25].[Na+:26].ClC=C(Cl)Cl>O1CCCC1>[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S:12]([C:13]2[N-:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=3[N:21]=2)=[O:24])=[N:4][CH:3]=1.[OH2:25].[Na+:26]

Participants

5

Reactant 3

HCID 6575TrichloroethyleneHCID 14798Sodium HydroxideHCID 178488147HCID 178488147, compound

Product 1

HCID 23681230HCID 23681230, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Omeprazole (1300 g; 3.77 mol) was added under vigorous mechanical stirring to a mixture of tetrahydrofurane (13 L) and 50% aqueous NaOH (296 g, 3.7 mol) and stirring was continued for 45 min. Trichloroethylene (5.7 L) was added and stirring was continued over night at room temperature. The mixture was cooled to +5° C. and then stirred for 3 h. The precipitate was filtered off and the filter cake was washed with trichloroethylene (5 L) and dried under reduced pressure at 50° C. giving omeprazole sodium salt (1314 g, 95%), m.p. 208-210 ° C.

Workup

  1. stirringstirring
  2. waitwas continued over night at room temperature
  3. temperatureThe mixture was cooled to +5° C.
  4. stirringstirred for 3 h
  5. filtrationThe precipitate was filtered off
  6. washthe filter cake was washed with trichloroethylene (5 L)
  7. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-3a34c67e91a04c1f8ecac679be2aa99c
Source dataset
uspto-grants-2001_03
Patent number
US06207188B1

Reaction notes

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