m-Chloroperbenzoic acid → HCID 13151640, compound

HRID 2290247Notes

Reaction equation

HRID 2290247 reaction equation
ClC1C=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)C=1.[CH2:12]([N:16]1[C:25](=[O:26])[C:24]2[N:23](CCC=C)[CH:22]=[N:21][C:20]=2[N:19]([CH2:31][CH2:32][CH2:33][CH3:34])[C:17]1=[O:18])[CH2:13][CH2:14][CH3:15]>C(Cl)(Cl)Cl>[CH2:12]([N:16]1[C:25](=[O:26])[C:24]2[N:23]([CH2:6][CH2:5][CH:4]3[O:10][CH2:8]3)[CH:22]=[N:21][C:20]=2[N:19]([CH2:31][CH2:32][CH2:33][CH3:34])[C:17]1=[O:18])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20157766HCID 20157766, compound

Product 1

HCID 13151640HCID 13151640, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

39.4 g of m-chloroperbenzoic acid (70% pure) were added to a solution of 42.7 g of 1,3-dibutyl-7-(3-butenyl)xanthine in 900 ml of chloroform within 15 minutes, with stirring. After stirring at room temperature for 27 hours, the mixture was washed with 10% strength sodium dithionite solution, saturated sodium bicarbonate solution and water, dried and evaporated under reduced pressure. The residue was chromatographed on a silica gel column with a mixture of methylene chloride/acetone (7:3, v:v) and recrystallized from petroleum ether.

Workup

  1. stirringAfter stirring at room temperature for 27 hours
  2. washthe mixture was washed with 10% strength sodium dithionite solution, saturated sodium bicarbonate solution and water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on a silica gel column with a mixture of methylene chloride/acetone (7:3, v:v)
  6. customrecrystallized from petroleum ether

Sources & evidence

ORD record
ord-270d66e259fc4faeb16f2d2ce2cffb6e
Source dataset
uspto-grants-1986_10
Patent number
US04616020

Reaction notes

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