Dimethyl Sulfoxide → HCID 19879312, compound

HRID 1885575Notes

Reaction equation

HRID 1885575 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]1[CH:15]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:12]1[CH2:13][OH:14].C(N(CC)CC)C>ClCCl>[O:11]1[CH:15]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:12]1[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19879318HCID 19879318, compound

Product 1

HCID 19879312HCID 19879312, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A solution of 0.6 ml of dimethyl sulfoxide in 2 ml of dichloromethane is added with stirring, at -60° C., to a solution of 0.37 ml of oxalyl chloride in 10 ml of dichloromethane in a nitrogen atmosphere. After the mixture has been stirred for 5 minutes at -60° C. there is added thereto, over a period of 20 minutes, a solution of 0.7 g of (2RS,3SR)-2,3-epoxy-3-(5-chlorothiophen-2-yl)-propanol according to d) in 10 ml of dichloromethane. After a further 20 minutes at -60° C. 1.3 ml of triethylamine is added, the mixture is allowed to come to room temperature, washed with water, and dried over sodium sulfate. Filtration and concentration by evaporation yields the crude title compound in the form of a dark viscous oil.

Workup

  1. additionthere is added
  2. waitover a period of 20 minutes
  3. waitAfter a further 20 minutes at -60° C
  4. customto come to room temperature
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and concentration
  8. customby evaporation

Sources & evidence

ORD record
ord-fd840043f160450ca68bdf4f7cafaecd
Source dataset
uspto-grants-1992_09
Patent number
US05145868

Reaction notes

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