Aluminium lithium hydride → 1-(苯并[B]噻吩-2-基)-N-甲基甲胺

HRID 1921021

反应方程式

HRID 1921021 反应方程式
[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][CH2:3][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1

参与物

4

反应物 2

HCID 21226445Aluminium lithium hydrideHCID 22593821HCID 22593821，化合物

产物 1

HCID 6931411-(苯并[B]噻吩-2-基)-N-甲基甲胺收率 99%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
0 °C

实验过程

To a stirred suspension of N-methyl benzothiophene-2-carboxamide (10.0 g, 52 mmole) in dry THF (75 mL) under argon was added a solution of 1.0 M LiAlH4 in THF (135 mL, 135 mmole) over 15 minutes. The reaction quickly became clear and was heated at reflux for 2 days. After cooling to 0° C. the reaction was carefully quenched with the sequential addition of H2O (5.1 mL), 15% NaOH in H2O (5.1 mL), and H2O (15.3 mL). The mixture was filtered through a pad of Celite® and the filter pad was rinsed with Et2O (50 mL). The filtrate was concentrated to afford the title compound (9.11 g, 99%) as a pale yellow oil which solidified in the freezer 1H NMR (400 MHz, CDCl3) δ 7.83 (d, J=7.3 Hz, 1H), 7.72 (d, J=7.3 Hz, 1H), 7.33 (m, 2H), 7.17 (s, 1H), 4.06 (s, 2H), 2.53 (s, 3H), 1.56 (br s, 1H).

后处理

  1. customThe reaction quickly became clear
  2. temperaturewas heated
  3. temperatureat reflux for 2 days
  4. customwas carefully quenched with the sequential addition of H2O (5.1 mL), 15% NaOH in H2O (5.1 mL), and H2O (15.3 mL)
  5. filtrationThe mixture was filtered through a pad of Celite®
  6. washthe filter pad was rinsed with Et2O (50 mL)
  7. concentrationThe filtrate was concentrated

来源与证据

ORD记录
ord-66be3d719b2e4cc78a64cb4a79b7b150
来源数据集
uspto-grants-2012_05
专利号
US08173646B2

关联笔记

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