三乙胺 → N-(5-甲基吡啶-2-基)新戊酰胺

HRID 17947

反应方程式

HRID 17947 反应方程式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.CCN(CC)CC.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>C(Cl)Cl>[CH3:16][C:17]([CH3:22])([CH3:21])[C:18]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)=[O:19]

参与物

5

反应物 3

HCID 8471三乙胺HCID 153482-氨基-5-甲基吡啶HCID 62493特戊酰氯

产物 1

HCID 4182924N-(5-甲基吡啶-2-基)新戊酰胺收率 98.4%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

To a stirred solution of 5-methylpyridin-2-amine (200 g, 1.85 mol) in anhydrous CH2Cl2 (1000 mL) was added dropwise a solution of Et3N (513 mL, 3.70 mol) and 2,2-dimethyl-propionyl chloride (274 mL, 2.22 mol) at 0° C. under N2. The ice bath was removed and stirring was continued at room temperature for 2 hours. The reaction was poured into ice (2000 g). The organic layer was separated and the remaining aqueous layer was extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4 and evaporated to afford 2,2-dimethyl-N-(5-methyl-pyridin-2-yl)-propionamide (350 g), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=8.4 Hz, 1H), 8.06 (d, J=1.2 Hz, 1H), 7.96 (s, 1H), 7.49 (dd, J=1.6, 8.4 Hz, 1H), 2.27 (s, 1H), 1.30 (s, 9H).

后处理

  1. customThe ice bath was removed
  2. additionThe reaction was poured into ice (2000 g)
  3. customThe organic layer was separated
  4. extractionthe remaining aqueous layer was extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. customevaporated

来源与证据

ORD记录
ord-799519345dc84116b566d7bd6ca28175
来源数据集
uspto-grants-2010_06
专利号
US07741321B2

关联笔记

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