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

HRID 76137Notes

Reaction equation

HRID 76137 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-10127b2c855b422fb590b1958f5b38b6
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

Loading…