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Ammonium Chloride → HCID 178482586、化合物

HRID 1357278
ノート
印刷プレビュー

反応式

HRID 1357278 の反応式
[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]#[N:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:30])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:29])[CH:21]=1)=[O:19])=[CH:7]2.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:33][N:32]=[N:31][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:30])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:29])[CH:21]=1)=[O:19])=[CH:7]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 120835741-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide

生成物 1

HCID 178482586HCID 178482586、化合物収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (1.0 g, 2.0 mmol), prepared in the previous step, sodium azide (0.32 g, 6.0 mmol) and ammonium chloride (0.39 g, 6.0 mmol) in 15 mL of DMF was stirred under nitrogen at 100° C. for 6 h. The reaction was partitioned between ethyl acetate and water. The aqueous layer was made basic by the addition of 1 N NaOH. The organic layer was separated and the aqueous layer extracted five times with ethyl acetate. The aqueous layer was then acidified with 1N HCl. After 2 h a white solid had precipitated from solution. The solid was collected by filtration and dried under reduced pressure to give the title compound (0.8460 g, 84%) as an off-white solid, mp 227-228° C.

後処理

  1. customThe reaction was partitioned between ethyl acetate and water
  2. additionThe aqueous layer was made basic by the addition of 1 N NaOH
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted five times with ethyl acetate
  5. customAfter 2 h a white solid had precipitated from solution
  6. filtrationThe solid was collected by filtration
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-f258b715facd431d81a5f5e4808e22e5
出典データセット
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06589970B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート