N-bromobutanimide → HCID 59446608, compound

HRID 2364045Notes

Reaction equation

HRID 2364045 reaction equation
[CH2:1]([C:3]1[N:7]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[N:6]=[CH:5][CH:4]=1)[CH3:2].[Br:14]N1C(=O)CCC1=O>C1COCC1>[Br:14][C:4]1[CH:5]=[N:6][N:7]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66743233HCID 66743233, compound

Product 1

HCID 59446608HCID 59446608, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 5-ethyl-N,N-dimethyl-1H-pyrazole-1-sulfonamide (19.8 g, 97 mmol) in THF (300 mL) was added 1-bromopyrrolidine-2,5-dione (20.8 g, 117 mmol). The mixture was stirred for 2 h at 50° C. The mixture was concentrated under reduced pressure, and the residue was poured into saturated aqueous NaHCO3. Extraction with EtOAc, washing with brine, drying over MgSO4, filtration and concentration under reduced pressure gave a yellow oil. This residue was purified by column chromatography (Purif, silica gel, hexane to 50:50 hexane/EtOAc) to afford the title compound (26.2 g, 95%) as a yellow oil:

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was poured into saturated aqueous NaHCO3
  3. extractionExtraction with EtOAc
  4. washwashing with brine
  5. dry with materialdrying over MgSO4, filtration and concentration under reduced pressure
  6. customgave a yellow oil
  7. customThis residue was purified by column chromatography (Purif, silica gel, hexane to 50:50 hexane/EtOAc)

Sources & evidence

ORD record
ord-f264664e3e184def994a0c15b1ea2c29
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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