Methyl iodide → HCID 57018081, compound

HRID 2254639Notes

Reaction equation

HRID 2254639 reaction equation
[OH:1][CH2:2]/[C:3](=[C:14]1\[C:15](=[O:20])[NH:16][C:17](=[O:19])[S:18]\1)/[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.[C:21](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O.C(Cl)(Cl)Cl>[OH:1][CH2:2][C:3](=[C:14]1[S:18][C:17](=[O:19])[N:16]([CH3:21])[C:15]1=[O:20])[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86747113HCID 86747113, compound

Product 1

HCID 57018081HCID 57018081, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

(E)-5-[2-Hydroxy-1-(1-naphthalenyl)ethylidene]-2,4-thiazolidinedione (1.49 g, 5.22 mmol) was added to suspension of potassium carbonate (7.22 g, 52.2 mmol) in acetone. After 30 minutes iodomethane (0.65 mL, 10.4 mmol) was added. After 30 min the mixture was filtered, and concentrated to give a brown oil which was dissolved in chloroform. The resulting solution was washed with water then dried over magnesium sulfate and concentrated in vacuo to give an oil which was chromatographed on silica gel (chloroform/acetonitrile) to give a glass (1.17 g). Recrystallization from carbon tetrachloride/hexane/ether gave analytically pure E isomer of the title compound as yellow needles (0.90 g).

Workup

  1. filtrationAfter 30 min the mixture was filtered
  2. concentrationconcentrated
  3. customto give a brown oil which
  4. washThe resulting solution was washed with water
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas chromatographed on silica gel (chloroform/acetonitrile)

Sources & evidence

ORD record
ord-c3c1c2366b8542d5a456a88dff4915c7
Source dataset
uspto-grants-1993_08
Patent number
US05236941

Reaction notes

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