Dimethyl Sulfoxide → HCID 25230336, compound

HRID 562952Notes

Reaction equation

HRID 562952 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH:15][CH:16]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][CH3:40])[CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:21][CH:20]=1.CS(C)=O.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:40][O:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:16](=[O:15])[CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 14812Phosphorus oxide (P4O10)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 469110385-{4-[2-Hydroxy-2-(2-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione

Product 1

HCID 25230336HCID 25230336, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of phosphorus pentoxide (0.30 g, 1.10 mmol) in DCM (8 ml) at 0° C. was added a solution of 5-{4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.20 g, 0.54 mmol) in DCM (8 ml) followed by dimethyl sulfoxide (0.20 mL, 2.80 mmol). After stirring for 15 minutes, N,N-diisopropylethylamine (0.28 mL, 1.60 mmol) was added. After 45 minutes, the reaction mixture was cast into cold saturated NaHCO3 and extracted with EtOAc (×2). The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was chromatographed on a small silica gel column eluting with 0-10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 175 mg (88%) of the title compound as a light yellow solid. MS (ESI−) for C19H17NO5S m/z 370.1 (M−H)−.

Workup

  1. waitAfter 45 minutes
  2. extractionextracted with EtOAc (×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on a small silica gel column
  8. washeluting with 0-10% EtOAc/DCM
  9. additionFractions containing product
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-523be4afe3594a4fb9302aea3a76ea3f
Source dataset
uspto-grants-2011_11
Patent number
US08067450B2

Reaction notes

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