Sodium Thiosulfate → HCID 178509362, compound

HRID 34076Notes

Reaction equation

HRID 34076 reaction equation
[NH:1]1[C:5]2[S:6][C:7]([C:9]#[N:10])=[CH:8][C:4]=2[CH:3]=[N:2]1.[Br:11]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Br:11][C:3]1[C:4]2[CH:8]=[C:7]([C:9]#[N:10])[S:6][C:5]=2[NH:1][N:2]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 689269941H-thieno[2,3-c]pyrazole-5-carbonitrile

Product 1

HCID 178509362HCID 178509362, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 168 mg of 1H-thieno[2,3-c]pyrazole 5-carbonitrile in 5 mL of dimethylformamide was added 200 mg of N-bromosuccinimide at room temperature and stirred at this temperature for 2 hours. After adding 1 mL of 10% sodium thiosulfate aqueous solution, the solution was diluted with ethyl acetate. The organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. This afforded 3.7 g of the title compound as a colorless oil. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10), to afford 220 mg of the title compound as colorless crystals.

Workup

  1. washThe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-d74b81334895499cb27a5f68d10fd98e
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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