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1,4-Dioxane hydrochloride → N-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl)hydrazinecarboxamide hydrochloride

HRID 1892519
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1892519
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:30]=[CH:29][C:15]([CH2:16][NH:17][C:18]([NH:20][NH:21]C(OC(C)(C)C)=O)=[O:19])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].O1CCOCC1.[ClH:37]>ClCCl>[ClH:37].[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:30]=[CH:29][C:15]([CH2:16][NH:17][C:18]([NH:20][NH2:21])=[O:19])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]
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Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86650019Tert-butyl 2-[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate

Produkt 1

HCID 86650020N-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl)hydrazinecarboxamide hydrochlorideAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of tert-butyl 2-[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate (281.8 mg, 0.65 mmol) in anhydrous dichloromethane (3.25 ml) was added 4M-hydrogen chloride dioxane solution (3.25 ml, 13.0 mmol). After stirring at room temperature for 1 hr, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was concentrated again under reduced pressure. The operation was performed 3 times to remove hydrogen chloride gas azeotropically. The residue was suspended in ethyl acetate and filtered. The filtered product was washed with ethyl acetate, and dried under reduced pressure to give the title compound (245.1 mg, quantitative) as a white solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. customto remove hydrogen chloride gas azeotropically
  5. filtrationfiltered
  6. washThe filtered product was washed with ethyl acetate
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1bed74c434a245de8a813303a37e9859
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08507690B2

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