Sodium Hydroxide → HCID 178488037, compound

HRID 559274Notes

Reaction equation

HRID 559274 reaction equation
[OH-].[Na+:2].[CH3:3][C:4]1[CH:5]=[N:6][C:7]([CH2:13][S+:14]([O-:26])[C:15]2[NH:16][C:17]3[CH:18]=[CH:19][C:20]([O:24][CH3:25])=[CH:21][C:22]=3[N:23]=2)=[C:8]([CH3:12])[C:9]=1[O:10][CH3:11]>CO>[CH3:3][C:4]1[CH:5]=[N:6][C:7]([CH2:13][S+:14]([O-:26])[C:15]2[N-:16][C:17]3[CH:18]=[CH:19][C:20]([O:24][CH3:25])=[CH:21][C:22]=3[N:23]=2)=[C:8]([CH3:12])[C:9]=1[O:10][CH3:11].[Na+:2]

Participants

4

Procedure

8.7 g of sodium hydroxide and 175 ml of methanol were taken into a round bottom flask and stirred for 15 minutes. A solution of 50 g of esomeprazole dissolved in 175 ml of methanol was added to the above methanolic sodium hydroxide. The mixture was stirred at 29° C. for 3.5 hours. The mixture was then distilled atmospherically at 78° C. to remove 80% of the solvent. 250 ml of ethyl acetate was added to the residue and was co-distilled with 750 ml of ethyl acetate in three equal lots at 40° C. To the obtained residue, another 250 ml of ethyl acetate was added and stirred at 29° C. for 1 hour. The separated solid was filtered and washed with 100 ml of ethyl acetate. The wet compound was taken into another round bottom flask and 250 ml of ethyl acetate was added and stirred for 1 hour, 15 minutes. The separated solid was filtered and washed with 100 ml of ethyl acetate. The wet compound was dried at 62° C. for 6 hours to yield 51.2 g of the title compound.

Workup

  1. stirringThe mixture was stirred at 29° C. for 3.5 hours
  2. distillationThe mixture was then distilled atmospherically at 78° C.
  3. customto remove 80% of the solvent
  4. addition250 ml of ethyl acetate was added to the residue
  5. customwas co-distilled with 750 ml of ethyl acetate in three equal lots at 40° C
  6. additionTo the obtained residue, another 250 ml of ethyl acetate was added
  7. stirringstirred at 29° C. for 1 hour
  8. filtrationThe separated solid was filtered
  9. washwashed with 100 ml of ethyl acetate
  10. customThe wet compound was taken into another round bottom flask
  11. addition250 ml of ethyl acetate was added
  12. stirringstirred for 1 hour, 15 minutes
  13. filtrationThe separated solid was filtered
  14. washwashed with 100 ml of ethyl acetate
  15. customThe wet compound was dried at 62° C. for 6 hours

Sources & evidence

ORD record
ord-3b6cac1458b14e6aa38939653198806b
Source dataset
uspto-grants-2011_11
Patent number
US08063074B2

Reaction notes

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