Propargyl bromide → 2-Phenyl-4-propargyl-1,3,4-thiadiazolin-5-one

HRID 486619

Reaktionsgleichung

Reaktionsgleichung von HRID 486619
[C:1]1([C:7]2[S:8][C:9](=[O:12])[NH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]#[CH:21]>CC(C)=O>[C:1]1([C:7]2[S:8][C:9](=[O:12])[N:10]([CH2:21][C:20]#[CH:19])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 2122775-Phenyl-1,3,4-thiadiazol-2(3H)-one

Produkt 1

HCID 53236882-Phenyl-4-propargyl-1,3,4-thiadiazolin-5-oneAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To the solution of 2-phenyl-1,3,4-thiadiazolin-5-one (3 g, 16.85 mmole) in dry acetone (30 ml) under nitrogen with magnetic stirring was added potassium carbonate (3 g, 22 mmole), followed by propargyl bromide (3 g, 80% in toluene, 20 mmole) at room temperature. The mixture was refluxed for one hour. The reaction mixture was cooled down to room temperature and the solid was filtered off by suction-filtration. The filtrate was diluted with ether (200 ml) and washed with water (2×50 ml) and brine. The organic layer was dried over sodium sulfate. After the drying agent was filtered off the filtrate was concentrated to about 5 ml. Hexane was added to precipitate out the product. The product was collected by suction-filtration and washed with a little hexane to afford 2 g of 2-phenyl-4-propargyl-1,3,4-thiadiazolin-5-one as a powder. m.p.=73°-75° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationthe solid was filtered off by suction-filtration
  3. additionThe filtrate was diluted with ether (200 ml)
  4. washwashed with water (2×50 ml) and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationAfter the drying agent was filtered off the filtrate
  7. concentrationwas concentrated to about 5 ml
  8. additionHexane was added
  9. customto precipitate out the product
  10. filtrationThe product was collected by suction-filtration
  11. washwashed with a little hexane

Quellen und Nachweise

ORD-Eintrag
ord-1c53e3e461cb4c2ab27028ef6c2e9227
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292762

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