Benzoyl Peroxide → HCID 18347198, compound

HRID 2269566Notes

Reaction equation

HRID 2269566 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[O:12][CH:13]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:25])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCOCC>[Br:25][C:13]1[O:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 70215195HCID 70215195, compound

Product 1

HCID 18347198HCID 18347198, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the product of Step 2 (100 mg), NBS (90 mg) and benzoyl peroxide in CCl4 (5 mL) was heated to reflux under a spotlight for 30 min. The mixture was cooled, diluted with Et2O (3 ml) and filtered. The filtrate was concentrated and the residue was purified by flash chromatrography, eluted with 15:1 hexane/EtOAc to give the title compound (120 mg).

Workup

  1. temperatureto reflux under a spotlight for 30 min
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash chromatrography
  6. washeluted with 15:1 hexane/EtOAc

Sources & evidence

ORD record
ord-4a5ca15df95442d3b76a9eebcebc47af
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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