Dimethylformamide → HCID 13605070, Verbindung

HRID 1380393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380393
[CH3:1][C:2]1[S:6][C:5]([C:7](=NO)[CH3:8])=[CH:4][CH:3]=1.[ClH:11].[NH2:12]O.P(Cl)(Cl)(Cl)=O.[CH3:19][N:20]([CH3:23])C=O>O.CCOCC>[CH3:1][C:2]1[S:6][C:19]2=[N:20][C:23]([Cl:11])=[C:7]([C:8]#[N:12])[CH:5]=[C:4]2[CH:3]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 268902HCID 268902, VerbindungHCID 443297Hydroxyamine hydrochloride2×

Produkt 1

HCID 13605070HCID 13605070, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A suspension was prepared from 25 g of 5-methyl-2-acetylthiophene oxime (obtained by reacting the appropriate ketone with hydroxylamine hydrochloride by standard procedures) and 250 ml of ether and this was cooled to 10° C. in an ice-bath. Phosphoryl chloride (80 ml) was then added to the stirred suspension over a period of 15 minutes. The mixture was then allowed to warm to room temperature over a period of 16 hours. Then, 21 g of dimethylformamide was added over 10 minutes and the mixture was heated to 110° C. to boil off the ether. Heating was continued at 110° C. for 3.5 hours and then 11.2 g of hydroxylamine hydrochloride was added in portions over 20 minutes. The mixture was cooled and poured into 700 ml of water and the precipitate which formed was collected by filtration. This was recrystallized from acetone to give 2-methyl-6-chlorothieno[2,3-b]pyridine-5-carbonitrile melting at about 171°-173° C.

Aufarbeitung

  1. customobtained
  2. temperatureto warm to room temperature over a period of 16 hours
  3. temperaturethe mixture was heated to 110° C.
  4. temperatureHeating
  5. temperatureThe mixture was cooled
  6. customthe precipitate which formed
  7. filtrationwas collected by filtration
  8. customThis was recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-896c235fb2ea47f9b84afddaaa27f0c3
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04581455

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