Thionyl Chloride → 1-Iodo-2-cyano-4-propoxy-benzene

HRID 76137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 76137
[I:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=O.O=S(Cl)Cl>CN(C=O)C>[I:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]#[N:6]

Komponenten

4

Edukt 2

HCID 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

To 1.40 g (4.59 mmol) 2-iodo-5-propoxy-benzamide in 40 mL DMF are added 1.67 mL (22.9 mmol) SOCl2 and the reaction mixture is stirred at 115° C. for 1 h. The reaction is quenched by the addition of water and extracted with EtOAc (3×). The combined organic layers are washed with water and brine, dried with Na2SO4 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. customThe reaction is quenched by the addition of water
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, heptane/EtOAc 100/0→60/40)

Quellen und Nachweise

ORD-Eintrag
ord-10127b2c855b422fb590b1958f5b38b6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835472B2

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