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

HRID 1838210
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HRID 1838210 반응식
[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
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참가 물질

5

반응물 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 187532003-Bromo-5-chloropyrazine-2-carbonitrile

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-90174f5ca9494acd9f1906a2531a3133
출처 데이터셋
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06673795B2

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