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Sodium Hydroxide → 4-Bromo-2-(1H-1,2,4-triazol-3-yl)aniline

HRID 2241872
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2241872
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8]C(=O)[N:6]3[N:13]=[CH:14][N:15]=[C:5]3[C:4]=2[CH:3]=1.[OH-].[Na+]>C(O)CO>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:8])=[C:4]([C:5]2[NH:6][N:13]=[CH:14][N:15]=2)[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 1357668559-Bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one

Produkt 1

HCID 620726444-Bromo-2-(1H-1,2,4-triazol-3-yl)anilineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a well stirred slurry of 9-bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one (32.0 g, 171 mmol) in ethylene glycol (146 mL) which was heated at 100° C., was added aqueous NaOH (32%, 22.4 ml, 241 mmol). The slurry was heated at 140° C. for 17.5 h. The resulting solution was cooled to 27° C. and the product began to crystallize. Water (146 mL) and 1-octanol (1.73 mL) were added and the pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL). The resulting slurry was stirred for 30 min, the solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (25.2 g, 87%) as a light yellow solid. MS: m/e=239.0/241.1 [M+H+].

Aufarbeitung

  1. temperatureThe resulting solution was cooled to 27° C.
  2. customto crystallize
  3. additionWater (146 mL) and 1-octanol (1.73 mL) were added
  4. additionthe pH of the suspension was adjusted to 6.5 by the slow addition of glacial acetic acid (14 mL)
  5. filtrationthe solid was collected by filtration
  6. washwashed with water and 2-propanol
  7. customDrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-daab98dffd67408aac8f244443f8185e
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07671048B2

Notizen zur Reaktion

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