o-Nitrobenzonitrile → 2-([2-(Benzyloxy)ethyl]sulfanyl}benzonitrile

HRID 337147ノート

反応式

HRID 337147 の反応式
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[CH2:12]([O:19][CH2:20][CH2:21][SH:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>CN(C=O)C.O>[CH2:12]([O:19][CH2:20][CH2:21][S:22][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 11922o-NitrobenzonitrileHCID 14797Potassium HydroxideHCID 14571805Ethanethiol, 2-(phenylmethoxy)-

生成物 1

HCID 666890492-([2-(Benzyloxy)ethyl]sulfanyl}benzonitrile収率 66.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of 2-nitrobenzonitrile (5.85 g) in DMF (20 mL) was treated with 2-(benzyloxy)ethanethiol (Example 320a, 6.64 g) and a solution of potassium hydroxide (3.76 g) in water (5 mL) was added dropwise under nitrogen. The resulting mixture was stirred at 0° C. for 2 h. The reaction was quenched with water and extracted into ethyl acetate. The combined organics were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified (SiO2 chromatography eluting with 50% diethyl ether in iso-hexane) to afford the subtitle compound as a solid (7.08 g).

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted into ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. wash(SiO2 chromatography eluting with 50% diethyl ether in iso-hexane)

出典と根拠

ORDレコード
ord-996ad24f1b9f48009a26dce37682b52d
出典データセット
uspto-grants-2014_11
特許番号
US08889692B2

反応ノート

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