Hydrochloric Acid → HCID 58127523, compound

HRID 1257334Notes

Reaction equation

HRID 1257334 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH2:15][N:16]3[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[N:17]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>O1CCCC1CCO.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH2:15][N:16]3[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[N:17]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58127481ethyl 1-{[4-(3-nitrophenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

Product 1

HCID 58127523HCID 58127523, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixed solution of the compound (250 mg, 0.70 mmol) obtained in Example 25a in tetrahydrofuran-ethanol (v/v=1/1, 7 ml) was added 2N aqueous sodium hydroxide solution (1.4 mL, 2.8 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N aqueous hydrochloric acid solution, saturated brine was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the produced crude title compound was recrystallized (ethyl acetate-hexane) to give the title compound (227 mg, 98%) as colorless crystals.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe produced crude title compound
  7. customwas recrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-9061f734bd114631a7553f945e0edb6a
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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