Benzoyl Peroxide → HCID 68581072, compound

HRID 2235549Notes

Reaction equation

HRID 2235549 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C:5]1[C:10]2[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH2:2][CH3:3].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.O>[Br:19][C:8]1[C:9]2[NH:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]=2[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:16][CH2:17][CH3:18])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68582639HCID 68582639, compound

Product 1

HCID 68581072HCID 68581072, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 7-dipropylamino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (200 mg, 0.809 mmol), N-bromosuccinimide (216 mg, 1.21 mmol) and catalytic amount of benzoylperoxide in carbon tetrachloride (20 ml) was refluxed for 60 h and diluted with water. The aqueous solution was extracted with dichloromethane. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting 30% ethyl acetate/n-hexane to afford 73 mg (28%) of the title compound.

Workup

  1. temperaturewas refluxed for 60 h
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography
  7. washeluting 30% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-c08e37bd8b3347fdbc022302931ff879
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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