Dimethyl Sulfoxide → HCID 19808146, compound

HRID 1681078Notes

Reaction equation

HRID 1681078 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][CH:29]2[CH2:33][CH2:32][CH:31](/[CH:34]=[CH:35]/[CH2:36][OH:37])[CH2:30]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl.O>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][CH:29]2[CH2:33][CH2:32][CH:31](/[CH:34]=[CH:35]/[CH:36]=[O:37])[CH2:30]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19808145HCID 19808145, compound

Product 1

HCID 19808146HCID 19808146, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-35 °C

Procedure

Dimethylsulfoxide (312 mg), oxalyl chloride (254 mg) and triethyl amine (600 mg) were added to the alcohol [prepared in (1)] dissolved in methylene chloride (5 ml). The mixture was stirred for 1 hour at -35° C. Water was added to the reaction mixture. The mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then evaporated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=7:3) to obtain the title compound (405 mg) having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-b9d397f46c7d453aa2e78ef7beecf951
Source dataset
uspto-grants-1992_12
Patent number
US05168101

Reaction notes

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