Water → 1-(8-Nonenyl)-3,7-dimethylxanthine

HRID 129879

Reaction equation

HRID 129879 reaction equation
[NH:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3].[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25].O>CS(C)=O>[CH2:25]([N:1]1[C:12](=[O:13])[C:11]2[N:9]([CH3:10])[CH:8]=[N:7][C:6]=2[N:4]([CH3:5])[C:2]1=[O:3])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 110199989-Bromo-1-nonene

Product 1

HCID 152306351-(8-Nonenyl)-3,7-dimethylxanthineYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of theobromine (17.64 g, 98 mmol) and sodium hydride (2.35 g, 98 mmol) in dimethylsulfoxide (250 ml) was stirred for 15 minutes. 9-Bromo-1-nonene (20.0 g, 98 mmol) was added and stirring continued for 3 days. The reaction mixture was poured into water (300 ml) and extracted with dichloromethane (4×200 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (2×150 ml), dried over sodium sulfate, and the solvents evaporated under vacuum. The residue was crystallized (dichloromethane-ether) to give 1-(8-nonenyl)-3,7-dimethylxanthine (24.34 g, 99% yield) as white crystals.

Workup

  1. stirringstirring
  2. waitcontinued for 3 days
  3. extractionextracted with dichloromethane (4×200 ml)
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (2×150 ml)
  5. dry with materialdried over sodium sulfate
  6. customthe solvents evaporated under vacuum
  7. customThe residue was crystallized (dichloromethane-ether)

Sources & evidence

ORD record
ord-d90b6f3488194e32b42d8f77400e7453
Source dataset
uspto-grants-1995_11
Patent number
US05470878

Linked notes

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