Acetone → HCID 178460885, compound

HRID 274864Notes

Reaction equation

HRID 274864 reaction equation
[C:1]1([C:7]2[S:8][C:9](=[O:15])[N:10](CC#C)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:16]N1C(=O)CCC1=O.[CH3:24][C:25]([CH3:27])=O>[N+]([O-])([O-])=O.[Ag+]>[C:1]1([C:7]2[SH:8]([CH2:24][C:25]#[CH:27])[C:9](=[O:15])[N:10]([I:16])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 120273N-IodosuccinimideHCID 53236882-Phenyl-4-propargyl-1,3,4-thiadiazolin-5-one

Product 1

HCID 178460885HCID 178460885, compound

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

To the solution of 2-phenyl-4-propargyl-1,3,4-thiadiazolin-5-one (1.6 g, 7.4 mmole) in dry acetone (25 ml) under nitrogen with magnetic stirring was added catalytic amount of silver nitrate 0.1 g, 0.58 mmole), followed by N-iodosuccinimide (1.85 g, 8.15 mmole). The reaction mixture was stirred at room temperature for 20 hours. The solid was filtered off by suction-filtration through a Celite filter. The filtrate was diluted with water (200 ml) and extracted with ethyl acetate (2×100 ml). The organic layer was washed with water (2×50 ml), brine, and dried over sodium sulfate. The drying agent was filtered off and the filtrate was concentrated to give a residue. The residue was triturated with hexane and the product was collected by suction-filtration to give 1.75 g as a semicrystalline compound. m.p.=117°-119 C. Proton NMR spectum showed the desired compound.

Workup

  1. filtrationThe solid was filtered off by suction-filtration through a Celite
  2. filtrationfilter
  3. additionThe filtrate was diluted with water (200 ml)
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. washThe organic layer was washed with water (2×50 ml), brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe drying agent was filtered off
  8. concentrationthe filtrate was concentrated
  9. customto give a residue
  10. customThe residue was triturated with hexane
  11. filtrationthe product was collected by suction-filtration
  12. customto give 1.75 g as a semicrystalline compound

Sources & evidence

ORD record
ord-80fd29476ade420b9517e2ce0ed35d72
Source dataset
uspto-grants-1995_02
Patent number
US05391561

Reaction notes

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