N-bromobutanimide → 2-Methoxy-4-(bromomethyl)-N-(methylsulfonyl)benzamide

HRID 512050Notes

Reaction equation

HRID 512050 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:4]=1[C:5]([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[O:6].C1C(=O)N([Br:24])C(=O)C1>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:15]=[C:14]([CH2:16][Br:24])[CH:13]=[CH:12][C:4]=1[C:5]([NH:7][S:8]([CH3:11])(=[O:9])=[O:10])=[O:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66667421HCID 66667421, compound

Product 1

HCID 666676882-Methoxy-4-(bromomethyl)-N-(methylsulfonyl)benzamideYield 57%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methoxy-4-methyl-N-(methylsulfonyl)benzamide (Preparation 24, 500 mg, 2.06 mmol), N-bromosuccimide (402 mg, 2.36 mmol), azobisisobutyronitrile (10 mg, 0.06 mmol) and carbon tetrachloride (20 mL) were combined and stirred at reflux under nitrogen, whilst being irradiated with light from a lamp for 1 hour. After cooling, the mixture was evaporated, the residue suspended in water (30 mL) and extracted with EtOAc (1×30 mL). The organic layer was separated, washed with saturated brine (2×20 mL), dried over sodium sulfate, filtered and evaporated to give a solid, which was triturated with diethyl ether:hexane (1:4) to yield the title compound as a white solid (375 mg, 57%).

Workup

  1. temperatureat reflux under nitrogen
  2. customwhilst being irradiated with light from a lamp for 1 hour
  3. temperatureAfter cooling
  4. customthe mixture was evaporated
  5. extractionextracted with EtOAc (1×30 mL)
  6. customThe organic layer was separated
  7. washwashed with saturated brine (2×20 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto give a solid, which
  12. customwas triturated with diethyl ether:hexane (1:4)

Sources & evidence

ORD record
ord-5302fb93da3946128a7d2e587e767166
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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