Water → 1-(16-Heptadecenyl)-3,7-dimethylxanthine

HRID 964552Notes

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](Cl)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31].O>CS(C)=O.O1CCCC1>[CH2:31]([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])[CH2:30][CH2:29][CH2:28][CH2:27][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

Conditions

Temperature: 60 °C

Procedure

To a suspension of sodium theobromine (2.02 g, 10.0 mmol) in dimethylsulfoxide/tetrahydrofuran (2:1, 30 ml) was added 16-heptadecenyl chloride and the reaction stirred for 16 hours at 60° C. The mixture was then poured into water (75 ml) and extracted with ethyl acetate (3×75 ml). The organic portions were combined, dried over magnesium sulfate and the solvent evaporated, leaving a cream-colored solid residue. Recrystallization of the residue from hot hexane resulted in 2.31 g of 1-(16-Heptadecenyl)-3,7-dimethylxanthine as a white solid (85% yield).

Workup

extractionextracted with ethyl acetate (3×75 ml)
dry with materialdried over magnesium sulfate
customthe solvent evaporated
customleaving a cream-colored solid residue
customRecrystallization of the residue from hot hexane

Sources & evidence

ORD record: ord-0b698d1bac1c4dcd9bd34a24099d4c4e
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770595

Reaction notes

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