Methyl 3-carbamoyl-5-iodobenzoate → Methyl 3-cyano-5-iodobenzoate

Reaktionsgleichung

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:14])[CH:13]=1)[C:8]([NH2:10])=O)=[O:4]>S(Cl)(Cl)=O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:13]=[C:12]([I:14])[CH:11]=[C:7]([C:8]#[N:10])[CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 3-methoxycarbonyl-5-iodobenzamide (2.5 g, 8.2 mmol) in thionyl chloride (2 mL) was heated for 2 hours at 90° C. The reaction mixture was cooled and concentrated in vacuo. Silica gel chromatography afforded 670 mg (29%) of methyl-3-cyano-5-iodobenzoate, as a white solid.

Aufarbeitung

temperatureThe reaction mixture was cooled
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-01a282057cd145df82dd93d6b4912426
Quelldatensatz: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06660753B2

Notizen zur Reaktion

Wird geladen…

Komponenten

Edukt 1

HCID 21942671Methyl 3-carbamoyl-5-iodobenzoate

Produkt 1

HCID 21942623Methyl 3-cyano-5-iodobenzoateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel