Dimethyl Sulfoxide → HCID 86595011, compound

HRID 2212083Notes

Reaction equation

HRID 2212083 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH3:7]S(C)=O.[C:11]1([S:17]([CH2:20][CH:21]([O:23]C2CC2)O)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([S:17]([CH:20]([O:5][CH:1]2[CH2:2][CH2:7]2)[CH:21]=[O:23])(=[O:18])=[O:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69663663HCID 69663663, compound

Product 1

HCID 86595011HCID 86595011, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (444 mg, 3.5 mmol) was added to a stirred solution of DMSO (312 mg, 4 mmmol) in dichloromethane (30 ml) with cooling from a dry ice/acetone bath, followed after 10 min by a solution of 2-(1-benzenesulfonyl)cyclopropyloxyethanol (625 mg, 2.8 mmol) in dichloromethane (5 ml). The resulting thick suspension was stirred a further 15 min prior to adding triethylamine (505 mg, 5 mmol), removing the cooling bath and stirring a further 1 h. The solution was then washed sequentially with water (15 ml), 10% aqueous citric acid (15 ml), saturated aqueous sodium hydrogen carbonate (15 ml), and brine (15 ml), before being dried (MgSO4), and evaporated to leave the product as a gum (585 mg), which was used without further purification.

Workup

  1. temperaturewith cooling from a dry ice/acetone bath
  2. customremoving the cooling bath
  3. stirringstirring a further 1 h
  4. washThe solution was then washed sequentially with water (15 ml), 10% aqueous citric acid (15 ml), saturated aqueous sodium hydrogen carbonate (15 ml), and brine (15 ml)
  5. dry with materialbefore being dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-ef0f0fc5fc42410291dc740bb95a7070
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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