Benzoyl Peroxide → HCID 15675820, compound

HRID 1533867Notes

Reaction equation

HRID 1533867 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:19][C:20]1[CH:21]=[N:22][N:23]2[C:28]3[N:29]([CH2:32][CH3:33])[CH2:30][CH2:31][C:27]=3[C:26]([CH3:34])=[N:25][C:24]=12>C1C=CC=CC=1>[Br:19][C:20]1[CH:21]=[N:22][N:23]2[C:28]3[N:29]([CH2:32][CH3:33])[CH:30]=[CH:31][C:27]=3[C:26]([CH3:34])=[N:25][C:24]=12

Participants

4

Reactant 2

HCID 7187Benzoyl PeroxideHCID 15675798HCID 15675798, compound

Product 1

HCID 15675820HCID 15675820, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.16 g (8.92 mmoles) of benzoyl peroxide were added to a solution of 2.50 g (8.89 mmoles) of 3-bromo-7,8-dihydro-8-ethyl-5-methyl-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (prepared as described in Example 8) dissolved in 30 ml of benzene, and the mixture was stirred for 2 hours. At the end of this time, the reaction mixture was washed with a 5% v/v aqueous solution of sodium bicarbonate and then with water, after which it was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with chloroform) and recrystallized from diisopropyl ether to afford 1.019 g (yield 41%) of the title compound as light yellow needles, melting at 113°-114° C.

Workup

  1. washAt the end of this time, the reaction mixture was washed with a 5% v/v aqueous solution of sodium bicarbonate
  2. dry with materialwith water, after which it was dried over anhydrous sodium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel (eluted with chloroform)
  5. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-36a7ec94a2c44cdb95fd38f8e4ff5e63
Source dataset
uspto-grants-1992_02
Patent number
US05086057

Reaction notes

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