Hydrochloric Acid → 1-[3-(Thiophen-2-yl)-1,2,4-thiadiazol-5-yl]piperazine

HRID 2263023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263023
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[S:8][N:7]=1.Cl.CCCCCC>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[S:8][N:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 68777852HCID 68777852, Verbindung

Produkt 1

HCID 687780151-[3-(Thiophen-2-yl)-1,2,4-thiadiazol-5-yl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl 4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxylate (4.30 g, 12.2 mmol) in ethyl acetate (70 ml) was added a solution of 4 N hydrochloric acid in ethyl acetate (35 ml), and the mixture was stirred at room temperature for 18 hours and half. Hexane (150 ml) was poured to the reaction mixture, and a solid was separated by filtration. The obtained solid was dissolved in an aqueous saturated sodium hydrogen carbonate solution, followed by stirring at room temperature for 2 hours. Water was poured to the reaction mixture, and the resulting solution was extracted with a mixed solution of ethyl acetate/tetrahydrofuran (1:1). The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 2.31 g (75.0%) of the desired product as a solid was separated by filtration.

Aufarbeitung

  1. customa solid was separated by filtration
  2. dissolutionThe obtained solid was dissolved in an aqueous saturated sodium hydrogen carbonate solution
  3. stirringby stirring at room temperature for 2 hours
  4. additionWater was poured to the reaction mixture
  5. extractionthe resulting solution was extracted with a mixed solution of ethyl acetate/tetrahydrofuran (1:1)
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionHexane was poured to the residue, and 2.31 g (75.0%) of the desired product as a solid
  10. customwas separated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0998712190424240b298dbbf0c85c229
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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