Acetic Acid → 2-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile

HRID 1868293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868293
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5]([C:11]#[N:12])=[CH:4][NH:3]1.C(O)(=O)C.[I:17]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[I:17][C:9]1[S:10][C:6]2[C:5]([C:11]#[N:12])=[CH:4][NH:3][C:2](=[O:1])[C:7]=2[CH:8]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 184465784-Oxo-4,5-dihydrothieno[3,2-c]pyridine-7-carbonitrile

Produkt 1

HCID 184465252-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrileAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile 24 (5 g, 28.4 mmol) in a 1:1 solution of acetic acid and DMF (18.4 mL) was added N-iodosuccinimide (12.8 g, 56.8 mmol). The reaction was warmed to 80° C. and stirred for 21 h. The reaction was diluted 10 fold with water and neutralized with aqueous sodium bicarbonate. The precipitate was filtered, washed with water and dried to provide 7.27 g of 25. 1H NMR (400 MHz, d6-DMSO) δ 12.45 (s, 1H), 8.25 (d, J=5 Hz, 1H), 7.77 (s, 1H).

Aufarbeitung

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-383d1c5e9262487e8e19ae0e92535074
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635695B2

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