3-乙氧基丙烯酰氯 → 3-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamide

HRID 472158笔记

反应方程式

HRID 472158 反应方程式
[CH3:1][C:2]1[N:3]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[CH2:14]([O:16][CH:17]=[CH:18][C:19](Cl)=[O:20])[CH3:15]>N1C=CC=CC=1>[CH2:14]([O:16][CH:17]=[CH:18][C:19]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[CH:8][CH:9]=1)=[O:20])[CH3:15]

参与物

4

反应物 2

HCID 30144293-乙氧基丙烯酰氯HCID 31574784-(2-甲基-1H-咪唑-1-基)苯胺

产物 1

HCID 672049713-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamide收率 92.1%

试剂、催化剂与溶剂 1

HCID 1049吡啶溶剂

反应条件

温度
0 °C

实验过程

4-(2-methyl-1H-imidazol-1-yl)aniline (40.7 g, 232 mmol; RN: 74852-81-6, Maybridge, J. Med. Chem., 48(6), 1729-1744; 2005) was dissolved in dry pyridine (290 mL), 3-ethoxyacryloyl chloride (36.1 g, 268 mmol) was then added dropwise at 0°/−10° C. The resulting mixture was stirred at 0° C. for 2 hours and at r.t. overnight. The reaction mixture was quenched with 100 mL of water, and pyridine was distilled i.v., the residue was taken up with water and the pH was adjusted to pH=10, by adding K2CO3, the resulting suspension was extracted with AcOEt and concentrated. The resulting solid was stirred with hexane and filtered to afford the title product (58 g; 92%). C15H17N3O2, MW: 271.32.

后处理

  1. customThe reaction mixture was quenched with 100 mL of water, and pyridine
  2. distillationwas distilled i.v
  3. additionby adding K2CO3
  4. extractionthe resulting suspension was extracted with AcOEt
  5. concentrationconcentrated
  6. stirringThe resulting solid was stirred with hexane
  7. filtrationfiltered

来源与证据

ORD记录
ord-32752ba40a4a416784d226bcd7e05e8b
来源数据集
uspto-grants-2014_01
专利号
US08633208B2

反应笔记

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