Acetonitrile → 5-Formyl-4-chlorothiophene-3-carbonitrile

HRID 1582924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582924
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]([CH:17]=[O:18])=[C:12]([Cl:16])[C:13]=1[C:14]#[N:15].C(#N)C>CN(C)C=O>[CH:17]([C:11]1[S:10][CH:9]=[C:13]([C:14]#[N:15])[C:12]=1[Cl:16])=[O:18]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 10906Tert-Butyl nitriteHCID 27376122-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile

Produkt 1

HCID 199353485-Formyl-4-chlorothiophene-3-carbonitrileAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

35 g (325 mmol) of tert-butyl nitrite were added dropwise at room temperature to a solution of 53.0 g (250 mmol) of 2-amino-4-chloro-5-formylthiophene-3-carbonitrile (the synthesis of this compound is described in Patent DB 3738910) in 600 ml of a 1:1 mixture of acetonitrile and dimethylformamide, during which process the temperature of the reaction mixture rose from 20° C. to 37° C. and vigorous evolution of gas began. The mixture was cooled to 25° C. and stirred for 7 hours at room temperature, the black solution was concentrated on a rotary evaporator under a high vacuum, the residue was purified by column chromatography (eluant dichloromethane), and 29 g (68%) of the desired compound were obtained as yellow oil. 1H NMR (270 MHz, DMSO-d6): δ=9.1 (s, 1H), 10.0 (s, 1H).

Aufarbeitung

  1. customthe synthesis of this compound
  2. customrose from 20° C. to 37° C.
  3. concentrationthe black solution was concentrated on a rotary evaporator under a high vacuum
  4. customthe residue was purified by column chromatography (eluant dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-305eea2c6e2144cf9d61b01ea03bb2e8
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740647B1

Notizen zur Reaktion

Wird geladen…