Azobisisobutyronitrile → HCID 19698363, compound

HRID 862587Notes

Reaction equation

HRID 862587 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[C:44]1(=[O:54])[NH:48][C:47](=[O:49])[C:46]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:45]12.[K].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)(Cl)Cl>[C:44]1(=[O:54])[N:48]([CH2:1][C:2]2[CH:3]=[C:4]([CH2:11][CH2:12][CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[C:47](=[O:49])[C:46]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:45]12

Participants

7

Reactant 5

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 19698390HCID 19698390, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19698363HCID 19698363, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of diethyl 2-(3-methyl-6-nitrophenyl)ethylmalonate (2.7 g, 8.35 mmol), N-bromosuccinimide (1.63 g, 9.19 mmol), and azobisisobutyronitrile (100 mg) in carbon tetrachloride (35 mL) was refluxed for 14 h, while 3×50 mg of AlBN were added every 3 h during the reaction. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (100 mL) and potassium phthalimide (1.3 g, 7.02 mmol) was added. The mixture was stirred for 5 h at 4°~50° C., poured into saturated sodium bicarbonate, and extracted with a 1:1 mixture of toluene and ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 4:1 hexane/ethyl acetate to give 580 mg of the title compound (15%).

Workup

  1. additionwere added every 3 h during the reaction
  2. customThe insoluble material formed
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in DMF (100 mL)
  6. extractionextracted with a 1:1 mixture of toluene and ethyl acetate
  7. washThe organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography with 4:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-2a5f9648899249d5b5db69f89d9be2db
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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