Dimethyl Sulfoxide → HCID 22493528, compound

HRID 1816307Notes

Reaction equation

HRID 1816307 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]1[C:13]([CH2:26]O)=[N:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[C:20]=2[N:21]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CCCCCC.O>[CH3:11][C:12]1[C:13]([CH3:26])=[N:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[C:20]=2[N:21]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22493589HCID 22493589, compound

Product 1

HCID 22493528HCID 22493528, compoundYield 100.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 923 μl of dimethylsulfoxide in 2 ml of dichloromethane was added dropwise to a solution of 797 μl of oxalyl chloride in 6 ml of dichloromethane at −60° C. under a nitrogen gas stream, followed by stirring for 5 minutes. To the reaction mixture, a solution of 1 g of 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylquinoxaline-2-methanol in 6 ml of dichloromethane was added dropwise and the resulting mixture was stirred for 15 minutes. Triethylamine (4.8 ml) was then added dropwise to the reaction mixture, followed by stirring for 5 minutes. After the reaction mixture was raised to room temperature and stirred for 15 minutes, water was added thereto. The resulting mixture was extracted with dichloromethane. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 10% ethyl acetate/n-hexane), whereby 940 mg of the title compound were obtained in the form of a pale yellow solid.

Workup

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. stirringby stirring for 5 minutes
  3. stirringstirred for 15 minutes
  4. extractionThe resulting mixture was extracted with dichloromethane
  5. washThe organic layer was successively washed with water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue so obtained

Sources & evidence

ORD record
ord-4cb76d440f3e4934a4b0bc26bec36009
Source dataset
uspto-grants-2005_04
Patent number
US06884808B2

Reaction notes

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