N-bromobutanimide → HCID 178470082, compound

HRID 2102258Notes

Reaction equation

HRID 2102258 reaction equation
[OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH:12]([CH3:14])[CH3:13])[N:3]=1.[Br:15]N1C(=O)CCC1=O>ClCCl>[Br:15][C:5]1[N:4]([CH:12]([CH3:13])[CH3:14])[N:3]=[C:2]([OH:1])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178469772Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylate

Product 1

HCID 178470082HCID 178470082, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-hydroxy-1-isopropylpyrazole-4-carboxylate (10.5 g) was dissolved in dichloromethane (100 mL) and to the stirred solution was added N-bromosuccinimide (14.1 g) under ice cooling. The reaction mixture was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give 5.9 g of the title compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-1f83431b0f7d4bb0a2940084453d2648
Source dataset
uspto-grants-2009_08
Patent number
US07576064B2

Reaction notes

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