Sodium Hydroxide → HCID 68410676, compound

HRID 2194730Notes

Reaction equation

HRID 2194730 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:11][C:12]1[CH:13]=[C:14]([S:18][C:19]2[N:23]([C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])[N:22]=[C:21]([C:32]([NH:34][CH3:35])=O)[CH:20]=2)[CH:15]=[CH:16][CH:17]=1.[OH-].[Na+]>O1CCCC1>[Br:11][C:12]1[CH:13]=[C:14]([S:18][C:19]2[N:23]([C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])[N:22]=[C:21]([CH2:32][NH:34][CH3:35])[CH:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 68409745HCID 68409745, compound

Product 1

HCID 68410676HCID 68410676, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of aluminum chloride (1.28 g) in tetrahydrofuran (15 mL) was slowly added lithium aluminum hydride (364 mg) at 0° C., and the mixture was stirred at the same temperature for 15 min. To the obtained suspension was added dropwise a solution of 5-[(3-bromophenyl)thio]-1-(2,5-difluorophenyl)-N-methyl-1H-pyrazole-3-carboxamide (1.35 g) in tetrahydrofuran (7 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. A 8 mol/L aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 1.18 g, 90%).

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f86f8a65d3ad4df69a0d0f726d17cdd4
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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