Ethyl isothiocyanate → (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide

HRID 444703ノート

反応式

HRID 444703 の反応式
[Cl:1][C:2]1[C:7]([C:8]([NH:12][CH:13]2[CH2:15][CH:14]2[CH2:16][CH3:17])=[CH:9][C:10]#[N:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:20]([N:22]=[C:23]=[S:24])[CH3:21]>CN(C)C=O>[Cl:1][C:2]1[C:7](/[C:8](/[NH:12][CH:13]2[CH2:15][CH:14]2[CH2:16][CH3:17])=[C:9](\[C:10]#[N:11])/[C:23](=[S:24])[NH:22][CH2:20][CH3:21])=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 10966Ethyl isothiocyanateHCID 24758Sodium hydrideHCID 767595953-(2-Chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile

生成物 1

HCID 58319378(2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide収率 29.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.15 g, 0.606 mmol, 1 eq.) in 2 ml of dimethyl formamide (DMF) was treated with NaH (60% in mineral oil, 0.029 g, 0.727 mmol, 1.2 eq.) and stirring allowed for 1 h. ethylisothiocyanate (0.105 g, 1.21 mmol, 2 eq.) was added and stirring continued overnight. The reaction was quenched with water and extracted with AcOEt. The organic layers were combined, dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide (0.059 g, 27% yield) as a white solid.

後処理

  1. stirringstirring continued overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with AcOEt
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-56cba9f2574e463ea54be08f4a4fb597
出典データセット
uspto-grants-2013_07
特許番号
US08476197B2

反応ノート

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