N-bromobutanimide → HCID 59446608, compound

HRID 1022905Notes

Reaction equation

HRID 1022905 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[N:15]([S:16]([N:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[N:14]=[CH:13][CH:12]=1)[CH3:10]>O1CCCC1>[Br:1][C:12]1[CH:13]=[N:14][N:15]([S:16]([N:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])[C:11]=1[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66743233HCID 66743233, compound

Product 1

HCID 59446608HCID 59446608, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1-Bromopyrrolidine-2,5-dione (20.8 g) was added to a stirring solution (300 mL) of 5-ethyl-N,N-dimethyl-1H-pyrazole-1-sulfonamide (19.8 g) in tetrahydrofuran at room temperature. The reaction system was heated to 50° C., stirred for 2 hr and concentrated under reduced pressure. The residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (26.2 g) as a yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was poured into saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customInsoluble material was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b22df248aaa54795b9029fc796bf9d63
Source dataset
uspto-grants-2014_05
Patent number
US08722660B2

Reaction notes

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