Benzoyl Peroxide → HCID 19977724, compound

HRID 742219Notes

Reaction equation

HRID 742219 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:19][O:20][N:21]1[C:29]2[C:24](=[N:25][C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:28]=2)[CH:23]=[CH:22]1.[Cl:40]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:19][O:20][N:21]1[C:29]2[C:24](=[N:25][C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:28]=2)[C:23]([Cl:40])=[CH:22]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 19958200HCID 19958200, compound

Product 1

HCID 19977724HCID 19977724, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

Benzoyl peroxide (0.91 g, 0.037 mol) is added to diethyl 1-methoxypyrrolo[3,2-b]pyridine-5,6-dicarboxylate (1.0 g, 0.003 mol) dissolved in (40 mL) carbon tetrachloride under a nitrogen atmosphere and the suspension stirred for ten minutes. N-Chlorosuccinimide (0.84 g, 0.0063 mol) is then added and the reaction heated at 60° C. for four hours. The mixtue is cooled to room temperature and the inorganics are removed by filtration. The organic mother liquors are washed with water and sodium bisulfite and concentrated in vacuo to an orange oil. The oil is flash chromatographed using hexanes and then 4:1 hexanes/ethyl acetate, giving the title product as an off-white solid in 51% yield, having a melting point 146°-148° C.

Workup

  1. temperatureThe mixtue is cooled to room temperature
  2. customthe inorganics are removed by filtration
  3. washThe organic mother liquors are washed with water and sodium bisulfite
  4. concentrationconcentrated in vacuo to an orange oil
  5. customchromatographed

Sources & evidence

ORD record
ord-dcdd7ba5be7b4c0eba37d05530032480
Source dataset
uspto-grants-1996_09
Patent number
US05554579

Reaction notes

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