Dimethyl Sulfoxide → HCID 19077438, compound

HRID 964547Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([N:24]1[C:33](=[O:34])[C:32]2[N:31]([CH3:35])[CH:30]=[N:29][C:28]=2[N:27]([CH3:36])[C:25]1=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>ClCCl.O>[O:11]=[C:12]([N:24]1[C:33](=[O:34])[C:32]2[N:31]([CH3:35])[CH:30]=[N:29][C:28]=2[N:27]([CH3:36])[C:25]1=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of oxalyl chloride (0.11 ml, 1.30 mmol) in dichloromethane (8 ml) at -78° C. was added dimethylsulfoxide (0.20 ml, 2.60 mmol) and over a 5 minute period l-(1 -hydroxydodecyl)-3,7-dimethylxanthine (0.40 g, 1.10 mmol) in dichloromethane (4 ml). The reaction was stirred at -78° C. for 30 minutes and after the addition of triethylamine (0.72 ml, 5.20 mmol), the reaction was allowed to warm to 25° C. over 30 minutes. Water (10 ml) was added, the organic phase separated and the aqueous phase washed with dichloromethane (10 ml). The organic portions were combined and dried with magnesium sulfate, and the solvent evaporated to give a slightly yellow solid. The crude yellow solid was recrystallized from hot hexane to obtain 0.32 g of a white solid, 1-(1-oxododecyl)-3,7-dimethylxanthine (80% yield).

Workup

temperatureto warm to 25° C. over 30 minutes
customthe organic phase separated
washthe aqueous phase washed with dichloromethane (10 ml)
dry with materialdried with magnesium sulfate
customthe solvent evaporated
customto give a slightly yellow solid
customThe crude yellow solid was recrystallized from hot hexane

Sources & evidence

ORD record: ord-c81538759da84d9b9986ee3a75174cb6
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770595

Reaction notes

Loading…