N-bromobutanimide → HCID 16753950, compound

HRID 897372Notes

Reaction equation

HRID 897372 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:7]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 16753949HCID 16753949, compound

Product 1

HCID 16753950HCID 16753950, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-fluoro-N,N,2-trimethylbenzenesulfonamide (5.20 g, 24.0 mmol) and N-bromosuccinimide (4.69 g, 26.4 mmol) in dry CCl4 (100 mL) was refluxed overnight under nitrogen. Cooled the reaction and filtered off the succinimide salts by vacuum filtration, washing with CCl4. The concentrated filtrate was dissolved in a minimal amount of ethyl acetate and purified on an Isco column (110 g silica) running a 0 to 20% EtOAc/Hexane gradient over 40 minutes. The collected fractions were concentrated in vacuo to afford the desired material as a yellow oil in a ratio of 3.5:1 with the starting material.

Workup

  1. temperaturewas refluxed overnight under nitrogen
  2. temperatureCooled
  3. customthe reaction
  4. filtrationfiltered off the succinimide salts
  5. filtrationby vacuum filtration
  6. washwashing with CCl4
  7. dissolutionThe concentrated filtrate was dissolved in a minimal amount of ethyl acetate
  8. custompurified on an Isco column (110 g silica)
  9. customover 40 minutes
  10. concentrationThe collected fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-d8f7aac57dcb4d8fb5b0dbdb7782523a
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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