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Dimethyl Sulfoxide → Azemiglitazone

HRID 1873818
Notes
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Reaction equation

HRID 1873818 reaction equation
[OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1.CS(C)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:26][O:25][C:21]1[CH:20]=[C:19]([C:2](=[O:1])[CH2:3][O:4][C:5]2[CH:18]=[CH:17][C:8]([CH2:9][CH:10]3[S:14][C:13](=[O:15])[NH:12][C:11]3=[O:16])=[CH:7][CH:6]=2)[CH:24]=[CH:23][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 469110405-{4-[2-Hydroxy-2-(3-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione

Product 1

HCID 25230266AzemiglitazoneYield 54%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 5-{4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.62 g, 1.7 mmol) in DCM (15 ml) was added DMSO (0.5 ml) and the solution was cooled to 0° C. Added phosphorus pentoxide (0.52 g, 1.8 mmol) followed by triethylamine (1.2 mL, 8.3 mmol). The reaction was allowed to slowly warm to RT. After 2 hours water was added and the phases were separated. The pH of the aqueous phase was adjusted to ca. 7 with 2M NaOH. The aqueous phase was extracted with EtOAc. The combined extracts 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 0.33 g (54%) of the title compound as a white solid. MS (ESI+) for C19H17NO5S m/z 372.0 (M+H)+. MS (ESI−) for C19H17NO5S m/z 370.1 (M−H)−.

Workup

  1. temperatureto slowly warm to RT
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined extracts 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-891d2d2479b341338fd67e1b17de3872
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08304441B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes