N-bromobutanimide → HCID 67260615, compound

HRID 2359080Notes

Reaction equation

HRID 2359080 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:11]=[CH:10][N:9]([CH2:12][CH:13]([CH3:15])[CH3:14])[N:8]=2)=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>CN(C)C=O>[Br:16][C:11]1[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:8][N:9]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67260785HCID 67260785, compound

Product 1

HCID 67260615HCID 67260615, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-chloro-2-thienyl)-1-isobutyl-1H-pyrazole (1 eq, 0.045 mol) in dry N,N-dimethylformamide (130 mL) was added N-bromosuccinimide (1.1 eq, 0.05 mol) slowly and the resulting mixture was stirred at room temperature for 3 h. After completion reaction monitored by TLC, the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined organics layer were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated to afford 12 g of 4-bromo-3-(5-chloro-2-thienyl)-1-isobutyl-1H-pyrazole (82% yield).

Workup

  1. customAfter completion reaction
  2. additionthe reaction mixture was poured into ice cold water
  3. extractionextracted with ethyl acetate
  4. washThe combined organics layer were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6d14ad882c6447f3bbb9e9eff59ab6cf
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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