Iodine → 5(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-iodophenyl)oxazolidin-2-one

HRID 1167496Notes

Reaction equation

HRID 1167496 reaction equation
[I:1]I.[S:3]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[O:14][C:13](=[O:15])[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11]2)=[N:4]1>C(#N)C.C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[S:3]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[O:14][C:13](=[O:15])[N:12]([C:16]3[CH:17]=[CH:18][C:19]([I:1])=[CH:20][CH:21]=3)[CH2:11]2)=[N:4]1

Participants

6

Reactant 2

HCID 807IodineHCID 699806285(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one

Product 1

HCID 699805285(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-iodophenyl)oxazolidin-2-oneYield 73.4%

Reagents, catalysts & solvents 3

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Iodine (0.67 g, 2.64 mmol) was added portionwise to a stirred solution of 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one (0.7 g, 2.53 mmol) and silver trifluoroacetate (0.727 g, 3.29 mmol) in acetonitrile (4 ml) and chloroforrn (6 ml). The mixture was stirred for 24 hours in the dark. The mixture was filtered and the filtrate evaporated. The residue was extracted with EtOAc and the extract washed with water, dilute ammonia (0.1 ml of 0.88SG ammonia in 25 ml water), water and brine, dried (Na2SO4) and evaporated to give the title product as a solid (0.749 g, 73%)

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. extractionThe residue was extracted with EtOAc
  4. washthe extract washed with water, dilute ammonia (0.1 ml of 0.88SG ammonia in 25 ml water), water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-69288cb7e31449a7bc7378ee776070a1
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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