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Ethanolamine → 3-Bromo-5-[(2-hydroxyethyl)amino]-2-pyrazinecarbonitrile

HRID 1838210
ノート
印刷プレビュー

反応式

HRID 1838210 の反応式
[CH2:1]([CH2:3][NH2:4])[OH:2].[Br:5][C:6]1[C:7]([C:13]#[N:14])=[N:8][CH:9]=[C:10](Cl)[N:11]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[Br:5][C:6]1[C:7]([C:13]#[N:14])=[N:8][CH:9]=[C:10]([NH:4][CH2:3][CH2:1][OH:2])[N:11]=1
参加物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 700EthanolamineHCID 81531DiisopropylethylamineHCID 187532003-Bromo-5-chloropyrazine-2-carbonitrile

生成物 1

HCID 187532053-Bromo-5-[(2-hydroxyethyl)amino]-2-pyrazinecarbonitrile収率 53.9%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

0.061 g (1.00 mmol) of ethanolamine were added slowly at room temperature to a solution of 0.218 g (1.0 mmol) of the 3-bromo-5-chloro-pyrazine-2-carbonitrile and 0.264 g (2.0 mmol) of N-ethyldiisopropylamine in 15.0 ml of dioxane. The reaction mixture was stirred at room temperature for 18 hours. It was subsequently poured into 50 ml of an ice/water/sodium hydrogen carbonate mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 100:0 to 95:5 v/v gradient of dichloromethane and methanol as the eluent giving 0.131 g (0.539 mmol, 53.9% of theory) of the 3-bromo-5-(2-hydroxy-ethylamino)-pyrazine-2-carbonitrile as yellow solid; m.p. 158-160° C.; MS: 243 (M)+.

後処理

  1. extractionextracted 3 times with 50 ml of ethylacetate
  2. dry with materialThe combined ethylacetate phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue formed
  5. customwas chromatographed on silica gel with a 100:0 to 95:5 v/v gradient of dichloromethane and methanol as the eluent

出典と根拠

ORDレコード
ord-90174f5ca9494acd9f1906a2531a3133
出典データセット
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06673795B2

反応ノート

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