Water → 1-(8-Nonenyl)-3,7-dimethylxanthine

HRID 367271

Reaction equation

HRID 367271 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+].CS([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28])(=O)=O.O>CS(C)=O.C(OCC)(=O)C>[CH2:28]([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])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=[CH2:20]

Participants

7

Reactant 4

HCID 962WaterHCID 5429TheobromineHCID 24758Sodium hydrideHCID 232879369-Methanesulfonyl-1-nonene

Product 1

HCID 152306351-(8-Nonenyl)-3,7-dimethylxanthine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Theobromine (1.98 g, 11 mmol) was added to a suspension of NaH (600 mg of a 50% mineral oil slurry, 12 mmol) in DMSO (15 ml). After 15 minutes, 9-methanesulfonyl-1-nonene, prepared according to the foregoing procedure (2.25 g, 11 mmol), was added and the reaction mixture stirred for 6 days at 25° C. The reaction mixture was poured into 60 ml of water and extracted with dichloromethane (3×50 ml). The organic portions were combined, dried with magnesium sulfate, and evaporated to give a dark oil. Chromatography over silica gel using an ethyl acetate eluant produced 810 mg of 1-(8-nonenyl)-3,7-dimethylxanthine, a colorless oil (26% yield).

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane (3×50 ml)
  3. dry with materialdried with magnesium sulfate
  4. customevaporated
  5. customto give a dark oil

Sources & evidence

ORD record
ord-9e0999aa8400423b940ee5d9810686bf
Source dataset
uspto-grants-2000_10
Patent number
US06133274

Linked notes

Loading…