Benzoyl Peroxide → HCID 15676627, compound

HRID 1653972Notes

Reaction equation

HRID 1653972 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]([N:35]1[C:39](=[O:40])[C:38]([CH:42]([CH3:44])[CH3:43])([CH3:41])[N:37]=[C:36]1[C:45]1[N:54]=[CH:53][C:52]([CH3:55])=[CH:51][C:46]=1[C:47]([O:49][CH3:50])=[O:48])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:27]([N:35]1[C:39](=[O:40])[C:38]([CH:42]([CH3:44])[CH3:43])([CH3:41])[N:37]=[C:36]1[C:45]1[N:54]=[CH:53][C:52]([CH2:55][Br:1])=[CH:51][C:46]=1[C:47]([O:49][CH3:50])=[O:48])(=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 15676626HCID 15676626, compound

Product 1

HCID 15676627HCID 15676627, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Solid N-bromosuccinimide (22.98 g, 0.129 mol) and benzoyl peroxide (3.12 g, 0.0129 mol) are added to a 25° C. solution of 2-(1-benzoyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylnicotinic acid, methyl ester (46.2 g, 0.117 mol) in carbon tetrachloride. The reaction mixture is heated at 70° C. for 16 hours, cooled to room temperature, diluted with methylene chloride, washed sequentially with 5% sodium metabisulfite solution and water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give an oil. The oil is chromatographed using silica gel and hexanes/ethyl acetate (3:1) to (1:1) as eluant to give the title compound as a yellow solid (19.64 g, 35%), mp 88°-119° C., identified by IR and NMR spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. washwashed sequentially with 5% sodium metabisulfite solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil is chromatographed

Sources & evidence

ORD record
ord-20339f416f0044388f45c1662393a9fa
Source dataset
uspto-grants-1995_04
Patent number
US05405827

Reaction notes

Loading…