Water → 1-(12-Tridecenyl)-3,7-dimethylxanthine

HRID 361545Notes

Reaction equation

HRID 361545 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].[Na].[CH2:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27].O>CS(C)=O>[CH2:27]([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])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

5

Reactant 3

HCID 962WaterHCID 1482626513-Bromotridec-1-eneHCID 66980828Theobromine sodium

Product 1

HCID 154868371-(12-Tridecenyl)-3,7-dimethylxanthineYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium theobromine (2.22 g, 11.0 mmol) in dimethylsulfoxide (25 mL) was added 12-tridecenyl bromide and the reaction stirred for 16 hours at 60° C. The mixture was then poured into water (80 mL) and extracted with dichloromethane (3×50 mL). The combined organic portions were washed with water (3×100 mL), dried using magnesium sulfate, and evaporated to give a gummy residue. Purification by column chromatography using an ethyl acetate/hexane eluant yields 1.89 g (50% yield) 1-(12-Tridecenyl)-3,7-dimethylxanthine (inventive compound no. 2555) as a white solid.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. washThe combined organic portions were washed with water (3×100 mL)
  3. customdried
  4. customevaporated
  5. customto give a gummy residue
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-1785aa6d8b18444aa6dd888bb9b991d5
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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