Cyanuric chloride → 4-Chlorothieno[2,3-b]pyridine-5-carbonitrile

HRID 1178613

Reaktionsgleichung

Reaktionsgleichung von HRID 1178613
[Cl:1][C:2]1[C:7]([C:8]([NH2:10])=O)=[CH:6][N:5]=[C:4]2[S:11][CH:12]=[CH:13][C:3]=12.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C)C=O>[Cl:1][C:2]1[C:7]([C:8]#[N:10])=[CH:6][N:5]=[C:4]2[S:11][CH:12]=[CH:13][C:3]=12

Komponenten

4

Edukt 2

HCID 7954Cyanuric chlorideHCID 111485614-Chlorothieno[2,3-B]pyridine-5-carboxamide

Produkt 1

HCID 114129074-Chlorothieno[2,3-b]pyridine-5-carbonitrileAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-chlorothieno[2,3-b]pyridine-5-carboxamide (145 mg, 0.68 mmol) and cyanuric chloride (200 mg, 1.08 mmol) in 5 mL of N,N-dimethylformamide is stirred at room temperature for 30 minutes. Ice is added to the reaction mixture and the resultant solids are collected by filtration washing with water to provide 84 mg of 4-chlorothieno[2,3-b]pyridine-5-carbonitrile as a white solid, mp 100–103° C.; 1H NMR (DMSO-d6) δ 7.66 (d, J=6 Hz, 1H), 8.26 (d, J=6 Hz, 1H), 9.03 (s, 1H); MS 195.0 (M+H)+.

Aufarbeitung

  1. additionIce is added to the reaction mixture
  2. filtrationthe resultant solids are collected by filtration
  3. washwashing with water

Quellen und Nachweise

ORD-Eintrag
ord-68cbe3a5969d4df98e87fabf9a0fb916
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276519B2

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