Water → HCID 15230636, compound

HRID 361493Notes

Reaction equation

HRID 361493 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].[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: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])[CH2:23][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

To a suspension of sodium hydride (461 mg, 19.2 mmol) in dimethylsulfoxide (30 mL) was added theobromine (3.45 g, 19.2 mmol). After 15 minutes, the 9-decenylmesylate (2.25 g, 11 mmol) was added and the reaction stirred 18 hours at 25° C., then at 100° C. for 40 minutes. The mixture was then poured into water (100 mL) and extracted with dichloromethane (3×50 mL). The combined organic portions were washed with saturated salt solution (60 mL) and dried over magnesium sulfate. The solvent was evaporated under vacuum to give a white solid residue. Recrystallization in ether yields 3.40 g (56% yield) 1-(9-decenyl)-3,7-dimethylxanthine (inventive compound no. 1563).

Workup

  1. waitat 100° C. for 40 minutes
  2. extractionextracted with dichloromethane (3×50 mL)
  3. washThe combined organic portions were washed with saturated salt solution (60 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under vacuum
  6. customto give a white solid residue
  7. customRecrystallization in ether

Sources & evidence

ORD record
ord-f249ca7098284a0da8c3e0da34262539
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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