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

HRID 405979

Reaktionsgleichung

Reaktionsgleichung von HRID 405979
[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-Dichloropyrimidine-5-carbaldehyde oxime (8g) was dissolved in CHCl3 (40 mL) and treated with SOCl2 (6 mL) for 2 h at rt. The solvent was removed and redissolved in DCM (5 mL). The solid was filtered and washed with DCM (5 mL). The filtrate was concd and purified by column chromatography on silica gel (dry loading, DCM/hexane, 3/1) to give 4,6-dichloropyrimidine-5-carbonitrile as a white solid.

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionredissolved in DCM (5 mL)
  3. filtrationThe solid was filtered
  4. washwashed with DCM (5 mL)
  5. custompurified by column chromatography on silica gel (dry loading, DCM/hexane, 3/1)

Quellen und Nachweise

ORD-Eintrag
ord-9fa181c8e34b4f3c9ff0d21fac8ae88f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754089B2

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