Phosphorus oxide (P4O10) → HCID 25230337, compound

HRID 1404652Notes

Reaction equation

HRID 1404652 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:39])[CH2:23][O:24][C:25]2[CH:38]=[CH:37][C:28]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[NH:32][C:31]3=[O:36])=[CH:27][CH:26]=2)[CH:19]=[CH:20][CH:21]=1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CS(C)=O>[Cl:15][C:16]1[CH:17]=[C:18]([C:22](=[O:39])[CH2:23][O:24][C:25]2[CH:38]=[CH:37][C:28]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[NH:32][C:31]3=[O:36])=[CH:27][CH:26]=2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 14812Phosphorus oxide (P4O10)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 46911037HCID 46911037, compound

Product 1

HCID 25230337HCID 25230337, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of phosphorus pentoxide (0.38 g, 130 mmol) in DCM (8 mL) at 0° C. was added a solution of 5-{4-[2-(3-chlorophenyl)-2-hydroxyethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.25 g, 0.66 mmol) in DCM (8 mL) followed by dimethyl sulfoxide (0.23 mL, 3.30 mL). After stirring for 15 minutes N,N-diisopropylethylamine (0.34 mL, 2.00 mmol) was added. After 45 minutes the reaction was poured into cold saturated NaHCO3 and the mixture was 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 0-15% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 117 mg (47%) of a white solid. MS (ESI−) for C18H14ClNO4S m/z 374.1 (M−H)−.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted 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 0-15% EtOAc/DCM
  9. additionFractions containing product
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-30e2962f28b04605b763d3680bcf0743
Source dataset
uspto-grants-2014_12
Patent number
US08912335B2

Reaction notes

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