6-Bromohexan-2-one → 1,3-Dibutyl-7-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

HRID 1578069Notes

Reaction equation

HRID 1578069 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[CH2:9]([N:13]1[C:22](=[O:23])[C:21]2[NH:20][CH:19]=[N:18][C:17]=2[N:16]([CH2:24][CH2:25][CH2:26][CH3:27])[C:14]1=[O:15])[CH2:10][CH2:11][CH3:12].[Na]>C(O)C>[O:8]=[C:6]([CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2][N:20]1[C:21]2[C:22](=[O:23])[N:13]([CH2:9][CH2:10][CH2:11][CH3:12])[C:14](=[O:15])[N:16]([CH2:24][CH2:25][CH2:26][CH3:27])[C:17]=2[N:18]=[CH:19]1

Participants

4

Reactant 2

HCID 250616-Bromohexan-2-oneHCID 70571579Sodium 1,3-dibutyl xanthine

Product 1

HCID 129534331,3-Dibutyl-7-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

21.5 g (0.12 mol) of freshly distilled 1-bromo-5-hexanone are dissolved in 200 ml of absolute ethanol in a 500 ml capacity flask, followed by the gradual dropwise addition at boiling temperature of 34.7 g (0.12 mol) of sodium 1,3-dibutyl xanthine dissolved in 200 ml of absolute ethanol. The solution is heated under reflux. The reaction is over after about 24 hours. Removal of the alcohol by distillation in a rotary evaporator leaves a solid white residue. This residue is introduced into an extraction tube in which it is extracted with petrol 40/80 in a Soxhlet apparatus until no more starting material can be detected. The petrol is distilled off in a rotary evaporator, leaving 25 g (0.069 mol) of 7-(5'-oxohexyl)-1,3-dibutyl xanthine, corresponding to 75% of the theoretical, based on the sodium 1,3-dibutyl xanthine reacted.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux
  3. customafter about 24 hours
  4. customRemoval of the alcohol
  5. distillationby distillation
  6. customin a rotary evaporator
  7. customleaves a solid white residue
  8. additionThis residue is introduced into an extraction tube in which it
  9. extractionis extracted with petrol 40/80 in a Soxhlet apparatus until
  10. distillationThe petrol is distilled off in a rotary evaporator

Sources & evidence

ORD record
ord-b3bee793895648708a4aec06bbba7e34
Source dataset
uspto-grants-1981_09
Patent number
US04291037

Reaction notes

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