Water → HCID 15230636, compound

HRID 1637657Notes

Reaction equation

HRID 1637657 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+].[CH2:16]([CH2:26]S([O-])(=O)=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=C.O>CS(C)=O>[CH2:24]([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])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:26]

Participants

6

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 23287948HCID 23287948, compound

Product 1

HCID 15230636HCID 15230636, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

Theobromine (3.45 g, 19.2 mmol) was added to a suspension (30 ml) of sodium hydride (461 mg, 19.2 mmol) in dimethylsulfoxide. After 15 minutes, the 9-decenylmesylate (2.25 g, 11 mmol) was added and the reaction stirred for 18 hours at 25° C., then for 40 minutes at 100° C. The mixture was then poured into water (100 ml) and extracted with three 50 ml aliquots of dichloromethane. The combined organic portions were washed with saturated salt solution (60 ml) and dried over magnesium sulfate. Evaporating the solvent under vacuum left a white solid residue. Recrystallization of the residue in ether produced 3.40 g of 1-(9-decenyl)-3,7-dimethylxanthine (56% yield).

Workup

  1. waitfor 40 minutes at 100° C
  2. extractionextracted with three 50 ml aliquots of dichloromethane
  3. washThe combined organic portions were washed with saturated salt solution (60 ml)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporating the solvent under vacuum
  6. waitleft a white solid residue
  7. customRecrystallization of the residue in ether

Sources & evidence

ORD record
ord-496f46c088a140cd9aa01f63438ee37b
Source dataset
uspto-grants-2000_03
Patent number
US06043250

Reaction notes

Loading…