Thionyl Chloride → 4,6-Dichloropyrimidine-5-carbonitrile

HRID 1616057

Reaktionsgleichung

Reaktionsgleichung von HRID 1616057
[Cl:1][C:2]1[C:7]([CH:8]=[N:9]O)=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.O=S(Cl)Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 760165164,6-Dichloro-5-pyrimidinecarbaldehyde oxime

Produkt 1

HCID 5993714,6-Dichloropyrimidine-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

4,6-Dichloro-5-pyrimidinecarbaldehyde oxime (8 g) was dissolved in CHCl3 (40 mL) and treated with SOCl2 (6 mL) for 2 h at rt. The solvent was removed and the residue was dissolved in DCM (5 mL). The resulting solid was filtered and washed with DCM (5 mL). The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography using DCM-hexane (3:1) to give 4,6-dichloro-5-pyrimidinecarbonitrile as a white solid.

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in DCM (5 mL)
  3. filtrationThe resulting solid was filtered
  4. washwashed with DCM (5 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ec6df45510648cf809b546909897e57
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765768B2

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