Sodium Hydroxide → HCID 178488037, compound
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- stirringThe mixture was stirred at 29° C. for 3.5 hours
- distillationThe mixture was then distilled atmospherically at 78° C.
- customto remove 80% of the solvent
- addition250 ml of ethyl acetate was added to the residue
- customwas co-distilled with 750 ml of ethyl acetate in three equal lots at 40° C
- additionTo the obtained residue, another 250 ml of ethyl acetate was added
- stirringstirred at 29° C. for 1 hour
- filtrationThe separated solid was filtered
- washwashed with 100 ml of ethyl acetate
- customThe wet compound was taken into another round bottom flask
- addition250 ml of ethyl acetate was added
- stirringstirred for 1 hour, 15 minutes
- filtrationThe separated solid was filtered
- washwashed with 100 ml of ethyl acetate
- 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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