Dimethyl Sulfoxide → HCID 18466676, compound

HRID 1601005Notes

Reaction equation

HRID 1601005 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]1([CH3:41])[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[C:22]2[N:21]=[C:20]3[C:15]([CH2:16][CH2:17][CH:18]([CH:29]([OH:40])[C:30]4[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=4)[C:19]3=[O:28])=[N:14][C:13]1=2.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][C:12]1([CH3:41])[CH2:25][CH2:24][C:23]([CH3:26])([CH3:27])[C:22]2[N:21]=[C:20]3[C:15]([CH2:16][CH2:17][CH:18]([C:29]([C:30]4[CH:31]=[CH:32][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:38][CH:39]=4)=[O:40])[C:19]3=[O:28])=[N:14][C:13]1=2

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18466815HCID 18466815, compound

Product 1

HCID 18466676HCID 18466676, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A solution of 0.2 ml of dimethyl sulfoxide in 1 ml of methylene chloride was dropped into a solution of 0.124 ml of oxalyl chloride in 10 ml of methylene chloride cooled to -60° C., followed by the stirring for 5 minutes. A solution of 0.5 g of methyl 4-[(3,4,6,7,8,9-hexahydro-6,6,9,9-tetramethyl-1(2H)-phenazinon-2-yl)hydroxymethyl]benzoate in 10 ml of methylene chloride was dropped into the solution prepared above. The obtained mixture was stirred for 15 minutes, followed by the dropwise addition of 0.954 ml of triethylamine. The temperature of the reaction mixture was raised to room temperature. The resulting mixture was stirred for 30 minutes, followed by the addition of water. The obtained mixture was extracted with methylene chloride. The organic phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel chromatography (developer: 5% ethyl acetate/hexane) to give 0.248 g of the title compound as a pale-yellow oil.

Workup

  1. customstirring for 5 minutes
  2. customprepared above
  3. temperatureThe temperature of the reaction mixture was raised to room temperature
  4. stirringThe resulting mixture was stirred for 30 minutes
  5. extractionThe obtained mixture was extracted with methylene chloride
  6. washThe organic phase was washed with water
  7. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in a vacuum
  9. customThe residue was purified by silica gel chromatography (developer: 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6dddc50470af46079f6d27405570db8e
Source dataset
uspto-grants-1999_11
Patent number
US05977125

Reaction notes

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