Water → HCID 23295871, compound

HRID 361531Notes

Reaction equation

HRID 361531 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].CS([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])(=O)=O.O>CS(C)=O>[CH2:30]([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])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 962WaterHCID 23295897HCID 23295897, compoundHCID 66980828Theobromine sodium

Product 1

HCID 23295871HCID 23295871, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium theobromine (6.00 g, 30.0 mmol) in dimethylsulfoxide (60 mL) was added 12-methanesulfonyl-1-dodecene and the reaction stirred for 16 hours at 60° C. The mixture was then poured into water (120 mL) and extracted with diethyl ether (2×100 mL). The organic portions were combined, dried using magnesium sulfate and evaporated to give a cream solid. Recrystallization from ethyl acetate/hexane 1:1 yields 6.97 g (67% yield) 1-(11-dodecenyl)-3,7-dimethylxanthine (inventive compound no. 2516) as a white solid.

Workup

  1. extractionextracted with diethyl ether (2×100 mL)
  2. customdried
  3. customevaporated
  4. customto give a cream solid
  5. customRecrystallization from ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-3b99d46d7b2847a18e391c7e79ec13d2
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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