Benzoyl Peroxide → HCID 66677293, compound

HRID 2404355Notes

Reaction equation

HRID 2404355 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:10].BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.Cl.[C:38]([O:42][C:43](=[O:47])[CH2:44][NH:45][CH3:46])([CH3:41])([CH3:40])[CH3:39].C([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O.O1CCOCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH2:1][N:45]([CH3:46])[CH2:44][C:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:47])=[C:3]([Cl:10])[CH:4]=1)#[N:7]

Participants

9

Reactant 5

HCID 7187Benzoyl PeroxideHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 888943-Chloro-p-toluonitrileHCID 11252350Sarcosine t-butyl ester hydrochloride

Product 1

HCID 66677293HCID 66677293, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-methyl-3-chlorobenzonitrile (4.69 g, 31 mmol), N-bromosuccinimide (6.04 g, 34.2 mmol) and benzoyl peroxide (0.750 g, 3.10 mmol) in ACN (20 mL) was heated under reflux for 18 hours. The reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of Na2CO3 and brine. The organic phase was dried (MgSO4) and concentrated under vacuum. A portion of the residue (1.0 g, 4.34 mmol) was treated with sarcosine tert-butyl ester hydrochloride (1.57 g, 8.69 mmol) and K2CO3 (2.39 g, 17.4 mmol) in dioxane (5 mL). The resulting mixture was heated at 100° C. for 2 hours, and then concentrated under vacuum. The residue was dissolved in a mixture of DCM and water, and then passed through a hydrophobic frit. The solvent was evaporated under vacuum to afford the title compound (0.952 g, 74%).

Workup

  1. temperatureunder reflux for 18 hours
  2. washwashed with a saturated aqueous solution of Na2CO3 and brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue was dissolved in a mixture of DCM and water
  7. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-be80ef2838f447fdbae3c7e661c88f57
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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