Dimethyl Sulfoxide → HCID 19077440, compound

HRID 964541Notes

Reaction equation

HRID 964541 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]([CH3:35])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:31](=[O:32])[C:30]2[N:29]([CH3:33])[CH:28]=[N:27][C:26]=2[N:25]([CH3:34])[C:23]1=[O:24].C(N(CC)CC)C>ClCCl.O>[O:11]=[C:12]([CH3:35])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:31](=[O:32])[C:30]2[N:29]([CH3:33])[CH:28]=[N:27][C:26]=2[N:25]([CH3:34])[C:23]1=[O:24]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15491147HCID 15491147, compound

Product 1

HCID 19077440HCID 19077440, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dimethylsulphoxide (102 mg; 1.3 mmol) was added dropwise to a solution of oxalyl chloride (91.7 mg; 0.72 mmol) in 5 ml of dry dichloromethane at -78° C. A solution of 1-(10-hydroxyundecanyl)-3,7-dimethylxanthine (0.23 g; 0.66 mmol) in 5 ml of dichloromethane was added and the resulting mixture stirred for 15 minutes. Triethylamine (0.332 mg; 3.29 mmol) was then added and the reaction warmed to room temperature. After stirring the reaction for an hour, the mixture was poured into 25 ml of water and extracted with 3×25 ml of dichloromethane. The combined organic extracts were successively washed with 1% hydrogen chloride (20 ml), saturated sodium bicarbonate solution (20 ml) and brine (20 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using a 20% hexane/ethyl acetate eluant, resulting in 150 mg of 1-(10-oxoundecanyl)-3,7-dimethylxanthine (65.8% yield).

Workup

  1. stirringAfter stirring
  2. customthe reaction for an hour
  3. extractionextracted with 3×25 ml of dichloromethane
  4. washThe combined organic extracts were successively washed with 1% hydrogen chloride (20 ml), saturated sodium bicarbonate solution (20 ml) and brine (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customwas further purified by flash chromatography over silica gel using a 20% hexane/ethyl acetate eluant

Sources & evidence

ORD record
ord-194a214ab138407cadf12b408ccf3b50
Source dataset
uspto-grants-1998_06
Patent number
US05770595

Reaction notes

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