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

HRID 76137ノート

反応式

HRID 76137 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
115 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-10127b2c855b422fb590b1958f5b38b6
出典データセット
uspto-grants-2014_09
特許番号
US08835472B2

反応ノート

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