N-bromobutanimide → HCID 178470082, compound

HRID 2102330Notes

Reaction equation

HRID 2102330 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:14])=[N:8][N:9]([CH:11]([CH3:13])[CH3:12])[CH:10]=1)=[O:5])[CH3:2].[Br:15]N1C(=O)CCC1=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:14])=[N:8][N:9]([CH:11]([CH3:13])[CH3:12])[C:10]=1[Br:15])=[O:5])[CH3:2]

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

3-Hydroxy-1-isopropylpyrazole-4-carboxylic acid ethyl ester (10.5 g) was dissolved in dichloromethane (100 mL), and N-bromosuccinimide (14.1 g) was added to the solution under ice cooling. The 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 the title compound (5.9 g)

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-239871e0407d422fa1cb5fe1152071ee
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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