Dimethyl Sulfoxide → HCID 19077435, compound

HRID 964548Notes

Reaction equation

HRID 964548 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:19][CH2:20][CH:21]([OH:44])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:40](=[O:41])[C:39]2[N:38]([CH3:42])[CH:37]=[N:36][C:35]=2[N:34]([CH3:43])[C:32]1=[O:33])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C>ClCCl>[CH2:11]([O:19][CH2:20][C:21](=[O:44])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:40](=[O:41])[C:39]2[N:38]([CH3:42])[CH:37]=[N:36][C:35]=2[N:34]([CH3:43])[C:32]1=[O:33])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18694217HCID 18694217, compound

Product 1

HCID 19077435HCID 19077435, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylsulfoxide (0.18 ml, 2.5 mmol) was added slowly by syringe to a stirring solution of oxalyl chloride (0.11 ml, 1.3 mmol) in dichloromethane (5 ml) at -780° C. After 2 minutes, a solution of 1-(11-octyloxy-10-hydroxyundecyl)-3,7-dimethylxanthine, prepared above (0.5 g, 1.0 mmol) in dichloromethane (15 ml) was added dropwise over 5 minutes. Stirring was continued at -78° C. for 45 minutes . Triethylamine (0.72 ml, 5.2 mmol) was added and the cold bath subsequently removed. After 20 minutes, water (25 ml) was added and the mixture was extracted with dichloromethane (3×50 ml). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (20 ml) and saturated aqueous salt solution (20 ml), and then dried over sodium sulfate. The solvents were evaporated under vacuum to give a thick oil which was purified by chromatography (silica/dichloromethane-5% methanol) to obtain 205 mg of 1-(11-octyloxy-10-oxoundecyl)-3,7-dimethylxanthine (43% yield).

Workup

  1. additionwas added dropwise over 5 minutes
  2. waitwas continued at -78° C. for 45 minutes
  3. customthe cold bath subsequently removed
  4. waitAfter 20 minutes
  5. additionwater (25 ml) was added
  6. extractionthe mixture was extracted with dichloromethane (3×50 ml)
  7. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate (20 ml) and saturated aqueous salt solution (20 ml)
  8. dry with materialdried over sodium sulfate
  9. customThe solvents were evaporated under vacuum
  10. customto give a thick oil which
  11. customwas purified by chromatography (silica/dichloromethane-5% methanol)

Sources & evidence

ORD record
ord-5dac05bb35be4613b6a78257472321ee
Source dataset
uspto-grants-1998_06
Patent number
US05770595

Reaction notes

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