Sodium hydride → 2-{2-[2-(Dimethylamino)ethoxy]ethoxy}pyridine-4-carbonitrile

HRID 557376

反応式

HRID 557376 の反応式
[CH3:1][N:2]([CH3:9])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][OH:8].[H-].[Na+].Cl[C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]=1>CN(C=O)C>[CH3:1][N:2]([CH3:9])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 743482-(2-(Dimethylamino)ethoxy)ethanolHCID 5686382-Chloro-4-cyanopyridine

生成物 1

HCID 222492252-{2-[2-(Dimethylamino)ethoxy]ethoxy}pyridine-4-carbonitrile収率 105.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

To a DMF (30 mL) solution of 2-[2-(dimethylamino)ethoxy]ethan-1-ol (3.33 g, 25 mmol) was added NaH (60% in mineral oil, 900 mg, 22.5 mmol, hexane washed) and heated at 50° C. for 2 h. The warm sodium alkoxide solution was added to 2-chloro-4-cyanopyridine (3.12 g, 22.5 mmol) in DMF (10 mL). After the addition, the reaction mixture was heated to 70° C. for 2 h, then DMF was removed in vacuo. The residue was partitioned between CH2Cl2/H2O. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give a light yellow oil (5.6 g). MS: 236 (M+1). Calc'd. for C12H17N3O2−235.29.

後処理

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated to 70° C. for 2 h
  3. customDMF was removed in vacuo
  4. customThe residue was partitioned between CH2Cl2/H2O
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1315c345c86847ebb850784add72261f
出典データセット
uspto-grants-2011_11
特許番号
US08058445B2

関連ノート

読み込み中…