Dimethyl Sulfoxide → HCID 23118281, compound

HRID 1987781Notes

Reaction equation

HRID 1987781 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N+:11]([C:14]1[C:15]([CH3:29])=[C:16]2[C:21](=[C:22]([CH3:25])[C:23]=1[CH3:24])[O:20][C:19]([CH2:27][OH:28])([CH3:26])[CH2:18][CH2:17]2)([O-:13])=[O:12].C(N(CC)CC)C>C(Cl)Cl.O>[N+:11]([C:14]1[C:15]([CH3:29])=[C:16]2[C:21](=[C:22]([CH3:25])[C:23]=1[CH3:24])[O:20][C:19]([CH:27]=[O:28])([CH3:26])[CH2:18][CH2:17]2)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23118299HCID 23118299, compound

Product 1

HCID 23118281HCID 23118281, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen flow at −60° C., 1.6 ml of oxalic acid dichloride was dissolved in 40 ml of methylene chloride and 3.1 ml of DMSO was added dropwise at −60° C., followed by stirring for 5 minutes. A solution prepared by dissolving 3.9 g of 6-nitro-2-hydroxymethyl-2,5,7,8-tetramethylchroman in 10 ml of methylene chloride was added dropwise under a nitrogen gas flow at −60° C., followed by stirring at −60° C. for 30 minutes. 12 ml of triethylamine was added at −60° C. and the temperature was gradually raised to room temperature, thereby to complete the reaction. After the completion of the reaction, the reaction solution was poured into water and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 3.4 g of the objective product as a crystal.

Workup

  1. customA solution prepared
  2. additionwas added dropwise under a nitrogen gas flow at −60° C.
  3. stirringby stirring at −60° C. for 30 minutes
  4. customthe reaction
  5. customAfter the completion of the reaction
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter removing magnesium sulfate
  10. filtrationby filtration
  11. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-d91ecb9cd9324893bf9bc498adb35da4
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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