Water → 6-chloro-1-cyanomethyl-1H-indole-3-carboxylic acid dimethylamide

HRID 23417

反応式

HRID 23417 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]#[N:13])=[CH:4][CH:3]=1.[Cl-].Cl[C:16](=[N+:18]([CH3:20])[CH3:19])Cl.[OH2:21]>C(#N)C>[CH3:19][N:18]([CH3:20])[C:16]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]([CH2:11][C:12]#[N:13])[CH:7]=1)=[O:21]

参加物

5

反応物 3

HCID 962WaterHCID 2723945Phosgeniminium chlorideHCID 22574096(6-Chloro-indol-1-yl)-acetonitrile

生成物 1

HCID 695457376-chloro-1-cyanomethyl-1H-indole-3-carboxylic acid dimethylamide収率 46%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (6-chloro-indol-1-yl)-acetonitrile (0.446 g, 2.34 mmole) in acetonitrile (30 ml) was added dichloromethylene dimethylammonium chloride (phosgene imminium chloride) (0.418 g, 2.57 mmole). The reaction mixture was brought to reflux for 14 h and then poured into water (100 ml). The mixture was extracted into ethyl acetate and purified by column chromatography (silica gel, hexane:ethyl acetate 3:7) to afford the desired 6-chloro-1-cyanomethyl-1H-indole-3-carboxylic acid dimethylamide (0.286 g, 46% yield) in addition to recovered starting material (0.173 g). Step 3

後処理

  1. temperatureto reflux for 14 h
  2. extractionThe mixture was extracted into ethyl acetate
  3. custompurified by column chromatography (silica gel, hexane:ethyl acetate 3:7)

出典と根拠

ORDレコード
ord-487712064d624761912cada6a7d74149
出典データセット
uspto-grants-2005_02
特許番号
US06852726B2

関連ノート

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