1-Bromopropane → (Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

HRID 517598Notes

Reaction equation

HRID 517598 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[NH:17][C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8].Br[CH2:25][CH2:26][CH3:27]>CN(C=O)C>[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[N:17]([CH2:25][CH2:26][CH3:27])[C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Product 1

HCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (93 mg, 0.60 mmol) was added to a solution of compound 2 (75 mg, 0.30 mmol) in 3 mL of anhydrous DMF at 0° C. After stifling of the reaction mixture for 20 min, a solution of 1-bromopropane (30 μL, 0.33 mmol) in 1 mL of anhydrous DMF was added and then the reaction mixture was stirred at room temperature overnight. The reaction was quenched by adding water and extracted with ethyl acetate. The ethyl acetate layer was washed with water (4×20 mL) and dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (15% ethyl acetate in hexanes) to afford 82 mg (93.9%) as a light-yellow solid.

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water (4×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica column chromatography (15% ethyl acetate in hexanes)
  9. customto afford 82 mg (93.9%) as a light-yellow solid

Sources & evidence

ORD record
ord-939dcc066a6046ebb1f4f823fb93bf45
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

Loading…