Water → HCID 23295974, compound

HRID 361497Notes

Reaction equation

HRID 361497 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][CH:24]=[CH2:25])(=O)=O.O.C(OCC)(=O)C.CCCCCC>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][CH:20]=[CH2:19]

Participants

6

Reactant 4

HCID 962WaterHCID 21226206Ethyl acetate hexaneHCID 23295870HCID 23295870, compoundHCID 66980828Theobromine sodium

Product 1

HCID 23295974HCID 23295974, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium theobromine (9.05 g, 50.0 mmol) in dimethylsulfoxide (90 mL) was added 7-methanesulfonyl-1-heptene (9.30 g, 48.2 mmol). The reaction was stirred for 16 hours at 60° C. The mixture was then poured into water (100 mL) and extracted with ethyl acetate (3×100 mL). The organic portions were combined, dried, and evaporated to give an orange solid. Chromatography (silica, ethyl acetate/hexane) yielded 6.50 g (47% yield) 1-(6-Heptenyl)-3,7-dimethylxanthine (inventive compound no. 1534) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. customdried
  3. customevaporated
  4. customto give an orange solid

Sources & evidence

ORD record
ord-696635abf8234077a4c14a62aa0ef9a4
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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