N-bromobutanimide → HCID 54724221, compound

HRID 1831892Notes

Reaction equation

HRID 1831892 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>ClCCl>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([Br:23])[C:9]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54724181HCID 54724181, compound

Product 1

HCID 54724221HCID 54724221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of N-benzyl-4-hydroxy-2-pyridone ((0.75 g, 3.7 mmol), NBS (0.7 g, 1.05 mmol) in dichloromethane was stirred at room temperature for 1.5 h under argon atmosphere. It was diluted with dichloromethane (25 mL), cooled and filtered. The solids were washed with dichloromethane and dried in vacuo. The filtrate and the washings were combined and washed with water, dried (Na2SO4), filtered, and concentrated to dryness. The resulting residue was washed with EtOAc, and dried in vacuo to give a combined mass of 0.65 g of the title compound as a white powder: 1H NMR (CD3OD) δ: 7.54 (d, 1H, J=7.6 Hz), 7.27 (m, 5H), 6.12 (d, 1H, J=7.6 Hz), 5.15 (s, 2H); ES-MS: m/z=280 (MH+).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe solids were washed with dichloromethane
  4. customdried in vacuo
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. washThe resulting residue was washed with EtOAc
  10. customdried in vacuo

Sources & evidence

ORD record
ord-aa3ddbd94a9c45b8b343858b91fc3022
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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