Water → 1-Iodo-2-cyano-4-propoxy-benzene

HRID 330837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330837
O=S(Cl)Cl.[I:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH3:18])=[CH:11][C:7]=1[C:8]([NH2:10])=O.O>CN(C=O)C>[I:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH3:18])=[CH:11][C:7]=1[C:8]#[N:10]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 666113302-Iodo-5-propoxy-benzamide

Produkt 1

HCID 666142061-Iodo-2-cyano-4-propoxy-benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

1.67 mL (22.9 mmol) SOCl2 are added to 1.40 g (4.59 mmol) 2-iodo-5-propoxy-benzamide (XXIX.1) in 40 mL DMF. The mixture is stirred at 115° C. for 1 h. After that time, water is added and the mixture is extracted with EtOAc (3×). The combined organic layers are washed with water and brine, dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, heptane/EtOAc 100/0→60/40).

Aufarbeitung

  1. extractionthe mixture is extracted with EtOAc (3×)
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by column chromatography (silica gel, heptane/EtOAc 100/0→60/40)

Quellen und Nachweise

ORD-Eintrag
ord-a0b5b6a789ff4f9f948b06fda70b774f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877754B2

Notizen zur Reaktion

Wird geladen…