Sodium Hydroxide → HCID 68409995, compound

HRID 2194729Notes

Reaction equation

HRID 2194729 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]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:22]=[C:21]([C:31]([NH:33][CH3:34])=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]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:22]=[C:21]([CH2:31][NH:33][CH3:34])[CH:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 68411361HCID 68411361, compound

Product 1

HCID 68409995HCID 68409995, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of aluminum chloride (763 mg) in tetrahydrofuran (8 mL) was slowly added lithium aluminum hydride (217 mg) at 0° C., and the mixture was stirred at the same temperature for 30 min. To the obtained suspension was added dropwise a solution of 5-[(3-bromophenyl)thio]-1-(2-chlorophenyl)-N-methyl-1H-pyrazole-3-carboxamide (595 mg) in tetrahydrofuran (2 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 522 mg, 91%).

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-b5b2f2a87fe346e49e4cf031cd63bd65
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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