Water → 1-(9-Octadecenyl)-3,7-dimethylxanthine

HRID 1637664

Reaction equation

HRID 1637664 reaction equation
[H-].[Na+].[NH:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O>CS(C)=O>[CH2:17]([N:3]1[C:14](=[O:15])[C:13]2[N:11]([CH3:12])[CH:10]=[N:9][C:8]=2[N:6]([CH3:7])[C:4]1=[O:5])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 802021-Bromo-9-octadecene

Product 1

HCID 537845551-(9-Octadecenyl)-3,7-dimethylxanthineYield 34.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (95%, 84 mg, 3.5 mmol) was added to a solution of theobromine (0.595 g, 3.2 mmol) in dimethylsulfoxide (15 ml). After 20 minutes of stirring, 1-bromo-9-octadecene (0.995 g, 3 mmol), prepared above, was added. After 6 hours of stirring at room temperature, the reaction mixture was warmed to 60° C. over 3 hours and then poured into a separatory funnel containing 50 ml of water. The reaction mixture was extracted with five 40 ml aliquots of dichloromethane. The organic extracts were combined, washed with water (50 ml) and brine (50 ml) and dried over anhydrous magnesium sulfate. Removing the solvent under reduced pressure resulted in a crude product further purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant, yielding 0.44 g of 1-(9-octadecenyl)-3,7-dimethylxanthine (34% yield).

Workup

  1. additionwas added
  2. stirringAfter 6 hours of stirring at room temperature
  3. additionpoured into a separatory funnel
  4. extractionThe reaction mixture was extracted with five 40 ml aliquots of dichloromethane
  5. washwashed with water (50 ml) and brine (50 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoving the solvent under reduced pressure
  8. customresulted in a crude product
  9. customfurther purified by flash chromatography over silica gel using a 30% acetone/petroleum ether eluant

Sources & evidence

ORD record
ord-864b427317fa46738e642906207ca2cf
Source dataset
uspto-grants-2000_03
Patent number
US06043250

Linked notes

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