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Sodium Hydroxide → 2-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile

HRID 1409311
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1409311
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([C:11]2[NH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[C:7]([F:16])[C:4]=1[C:5]#[N:6].[OH-].[Na+]>C1COCC1>[Cl:2][C:3]1[CH:10]=[C:9]([C:11]2[NH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[C:7]([F:16])[C:4]=1[C:5]#[N:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 709807222-Chloro-6-fluoro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride

Produkt 1

HCID 671697812-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrileAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Chloro-6-fluoro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride (201 mmol, 51.8 g) was dissolved in THF (510 ml). Sodium hydroxide 50% (401 mmol, 32.1 g) was added and the resulting mixture was stirred at RT for 3 h. Almost all the solvents were evaporated and water was added to the residue. The mixture was stirred overnight at RT. The precipitate was removed by filtration the solid was flushed twice with water. The solid was dried under vacuum. 35.8 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 7.05 (d, 1H), 7.88-7.97 (m, 2H), 8.02-8.07 (m, 1H), 13.37 (bs, 1H).

Aufarbeitung

  1. customAlmost all the solvents were evaporated
  2. additionwater was added to the residue
  3. stirringThe mixture was stirred overnight at RT
  4. customThe precipitate was removed by filtration the solid
  5. customwas flushed twice with water
  6. customThe solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5ad683de8ee8439bae3d68b9104896b2
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08921378B2

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