Benzoyl Peroxide → HCID 19698387, compound

HRID 862593Notes

Reaction equation

HRID 862593 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH3:19])[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[N-:46]=[N+:47]=[N-:48].[Na+]>C(Cl)(Cl)(Cl)Cl.[Cl-].[Na+].O>[N:46]([CH2:19][C:12]1[CH:13]=[CH:14][C:15]([N+:16]([O-:18])=[O:17])=[C:10]([O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:11]=1)=[N+:47]=[N-:48]

Participants

7

Reactant 4

HCID 7187Benzoyl PeroxideHCID 33557Sodium AzideHCID 67184N-bromobutanimideHCID 19698357HCID 19698357, compound

Product 1

HCID 19698387HCID 19698387, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-tert-butoxycarbonylmethoxy-4-nitrotoluene (36.1 g, 120 mmol), N-bromosuccinimide (21.3 g, 120 mmol), and benzoyl peroxide (4 g) in carbon tetrachloride (500 mL) was refluxed for 18 h. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (10 mL) and sodium azide (5.2 g, 80 mmol) was added. The mixture was stirred for 2 h at 50° C., poured into brine, 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 9:1 to 7:3 hexane/ethyl acetate to give 13.4 g of the title compound (36%).

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe insoluble material formed
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in DMF (10 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 9:1 to 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-2c3e22935a784dd9841323400c188809
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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