N-bromobutanimide → HCID 12459834, compound

HRID 2199484Notes

Reaction equation

HRID 2199484 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([CH3:15])[C:4]=1[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:15][C:9]1[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 601782Methyl 2,4-dimethoxy-6-methylbenzoate

Product 1

HCID 12459834HCID 12459834, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Dissolve compound 3 (10 g, 0.0476 mol) in 50 ml carbon tetrachloride, heat to reflux under nitrogen protection, add portion wise a mixture of NBS (8.5 g, 0.0476 mol) and BPO (0.11 g, 0.476 mmol), after finishing the addition, reflux to react for 1 h. Then stop the reaction, cool and filter the mixture, spin-dry filtrate to obtain a pale yellow solid, re-crystallize from ethanol to obtain 11.3 g white solid (82%). 1H-NMR (400M, CDCl3) δ (ppm): 3.85 (s, 3H), 3.93 (s, 3H), 3.96 (s, 3H), 4.66 (s, 2H), 6.47 (s, 1H), 6.74 (s, 1H).

Workup

  1. temperatureheat
  2. temperatureto reflux under nitrogen protection
  3. additionadd portion wise
  4. additionthe addition
  5. temperaturereflux
  6. customto react for 1 h
  7. customthe reaction
  8. temperaturecool
  9. filtrationfilter the mixture, spin-dry filtrate
  10. customto obtain a pale yellow solid
  11. customre-crystallize from ethanol

Sources & evidence

ORD record
ord-47bfdebc3080426bbd98248811b517ee
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

Loading…