Dimethyl Sulfoxide → HCID 25230265, compound

HRID 1404629Notes

Reaction equation

HRID 1404629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.CS(C)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:25])[CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 46911042HCID 46911042, compound

Product 1

HCID 25230265HCID 25230265, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 5-{4-[2-(4-fluorophenyl)-2-hydroxyethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.52 g, 1.40 mmol) in DCM (15 mL) was added DMSO (0.5 mL) and the solution was cooled to 0° C. Phosphorus pentoxide (0.41 g, 1.44 mmol) was added followed by triethylamine (0.90 mL, 6.48 mmol). The reaction was allowed to slowly warm to RT and then stirred for 5 hours. The reaction mixture was partitioned between DCM and H2O, and the aqueous phase was extracted with DCM. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting white solid was chromatographed on a small silica gel column eluting with 10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.25 g (48%) of the title compound as a white solid. MS (ESI+) for C18H14FNO4S m/z 359.9 (M+H)+. MS (ESI−) for C18H14FNO4S m/z 358.0 (M−H)−.

Workup

  1. temperatureto slowly warm to RT
  2. customThe reaction mixture was partitioned between DCM and H2O
  3. extractionthe aqueous phase was extracted with DCM
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting white solid was chromatographed on a small silica gel column
  9. washeluting with 10% EtOAc/DCM
  10. additionFractions containing product
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-8abfaf9380da4b879d91a9895bb4833b
Source dataset
uspto-grants-2014_12
Patent number
US08912335B2

Reaction notes

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