Phosphorus oxide (P4O10) → HCID 25230337, compound

HRID 1873826Notes

Reaction equation

HRID 1873826 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, 1.30 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 mml). 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 sat'd NaHCO3 and the mixture was extracted with EtOAc (x2). 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 (x2)
  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-cbc3b355671745c1a754b9950ebb2a56
Source dataset
uspto-grants-2012_11
Patent number
US08304441B2

Reaction notes

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