Hydrochloric Acid → 5-[1-(5-Benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methyl]thiazolidine-2,4-dione

HRID 1811452Notes

Reaction equation

HRID 1811452 reaction equation
[CH2:1]([N:8]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2[CH:13]=[C:12]([CH:23]=[C:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[BH4-].[Li+].Cl>C1COCC1>[CH2:1]([N:8]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2[CH:13]=[C:12]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 4148881Lithium borohydrideHCID 866139515-[1-(5-Benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methylidene]thiazolidine-2,4-dione

Product 1

HCID 866139525-[1-(5-Benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methyl]thiazolidine-2,4-dioneYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

620 mg of 5-[1-(5-benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methylidene]thiazolidine-2,4-dione was dissolved in 2.31 ml of THF. 2.31 ml of pyridine and 2.31 ml of a THF solution of 2 M lithium borohydride were added to the solution, followed by heating and refluxing for 4 hours. The reaction liquid was cooled, acidified with diluted hydrochloric acid, and extracted with dichloromethane. The organic layer was washed with water, then with saturated sodium chloride solution, and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, the residue was crystallized using dichloromethane, and the solid thus obtained was separated by filtration. The solid separated by filtration was air-dried, giving 232 mg (36% yield) of 5-[1-(5-benzyl-6-oxo-5,6-dihydrophenanthridin-2-yl)methyl]thiazolidine-2,4-dione as white crystals.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 4 hours
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialwith saturated sodium chloride solution, and dried over sodium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe residue was crystallized
  11. customthe solid thus obtained
  12. customwas separated by filtration
  13. customThe solid separated by filtration
  14. customwas air-dried

Sources & evidence

ORD record
ord-9d3c33e3b4d94200a35b122c7037ade2
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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