Hydrochloric Acid → 4-(2-Oxopiperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamide

HRID 1696105Notes

Reaction equation

HRID 1696105 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[CH2:9][N:8](C(=O)C(F)(F)F)[CH2:7][CH2:6][N:5]1[C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>O>[O:3]=[C:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)(=[O:24])=[O:23])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594665024-(2-Oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 594656314-(2-Oxopiperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamideYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of sodium hydroxide (1.38 g, 34.5 mmol), and H2O (5.0 mL), at 0° C., was added 4-(2-oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (5.0 g, 11.5 mmol) portionwise over 10 minutes. The mixture was stirred at ambient temperature for 30 minutes. The solution was cooled to 0° C. followed by the addition of 1.0 N HCl aqueous solution (34.5 mL, 34.5 mmol). The light yellow solution was azeotroped with MeOH (4×100 mL) at <30° C. The obtained solid was suspended in 50% MeOH in CH2Cl2 (200 mL) and stirred for 5 minutes. The mixture was filtered and the filtrate was evaporated to give the desired amine as light yellow solid (2.5 g, 7.4 mmol, 64% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=339.3; tR=0.51 min.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customThe light yellow solution was azeotroped with MeOH (4×100 mL) at <30° C
  3. stirringstirred for 5 minutes
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b416ffa1790b4a0d8e6412822ec040dc
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Reaction notes

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