Triethylamine → (E)-N-(2-azidoethyl)-2-methyl-3-phenylacrylamide

HRID 2283579ノート

反応式

HRID 2283579 の反応式
[CH3:1]/[C:2](=[CH:6]\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)/[C:3]([OH:5])=O.C(Cl)(=O)C(Cl)=O.[N:19]([CH2:22][CH2:23][NH2:24])=[N+:20]=[N-:21].C(N(CC)CC)C>ClCCl>[N:19]([CH2:22][CH2:23][NH:24][C:3](=[O:5])/[C:2](/[CH3:1])=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:20]=[N-:21]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 65578Oxalyl chlorideHCID 637817alpha-Methylcinnamic acid

生成物 1

HCID 57914355(E)-N-(2-azidoethyl)-2-methyl-3-phenylacrylamide収率 96.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a 25 mL round-bottomed flask equipped with a magnetic stir bar was added (E)-2-methyl-3-phenylacrylic acid (0.0.512 g, 3.15 mmol) and dichloromethane (10 mL). Oxalyl chloride (0.400 g, 3.15 mmol) was added dropwise to the reaction mixture and allowed to stir for one hour. Then, the reaction mixture was concentrated de vacuo. To the crude mixture was then added dichloromethane (10 mL), 2-azidoethanamine (0.299 g, 3.47 mmol) and then triethylamine (0.351 g, 3.47 mmol) and allowed to stir for two hours. The reaction mixture was then concentrated de vacuo and then purified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane) to give (E)-N-(2-azidoethyl)-2-methyl-3-phenylacrylamide (0.698 g, 96% yield). 1H NMR (300 MHz, CDCl3) δ 7.39 (m, 6H), δ 7.01 (s, 1H), δ 3.51 (t, 2H), δ 3.45 (t, 2H), δ 2.13 (s, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 170.5, 136.2, 134.5, 132.0, 130.3, 129.6, 128.9, 128.6, 128.3, 50.9, 39.8, 14.5 ppm; HRMS (ESI) calcd for C12H14N4O (M+) 230.1168. Found 230.1165.

後処理

  1. customTo a 25 mL round-bottomed flask equipped with a magnetic stir bar
  2. concentrationThen, the reaction mixture was concentrated de vacuo
  3. stirringto stir for two hours
  4. concentrationThe reaction mixture was then concentrated de vacuo
  5. custompurified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane)

出典と根拠

ORDレコード
ord-737c98788f874d9fb17a2bbab3bfdf56
出典データセット
uspto-grants-2015_09
特許番号
US09145395B2

反応ノート

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