Acetic Acid → 6-(6-Bromo-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

HRID 532630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532630
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:17][C:13]3[S:14][CH:15]=[CH:16][C:12]=3[C:11]2=O)=O)=[CH:4][CH:3]=1.O.[NH2:20][NH2:21].C(O)(=O)C>C(O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:10]3[CH2:17][C:13]4[S:14][CH:15]=[CH:16][C:12]=4[C:11]=3[NH:21][N:20]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 866992295-(6-Bromo-pyridine-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

Produkt 1

HCID 718150976-(6-Bromo-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

5-(6-Bromo-pyridine-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.29 g, 4 mmol), hydrazine monohydrate (0.6 mL, 12 mmol), glacial acetic acid (1.4 mL) and ethanol (20 mL) were heated at 100° C. under nitrogen for 4 hr. The mixture was cooled to 25° C. and concentrated under reduced pressure to give a solid which was recrystallized from ethanol to provide the corresponding 6-(6-Bromo-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.83 g, 2.6 mmol) as white solid in 65% yield.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customto give a solid which
  3. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-273d05d580a848b08c05ff5c8964cff2
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853207B2

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