3-Ethoxy-2-propenoyl chloride → 3-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamide

HRID 472158

反応式

HRID 472158 の反応式
[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]

参加物

4

反応物 2

HCID 30144293-Ethoxy-2-propenoyl chlorideHCID 31574784-(2-methyl-1H-imidazol-1-yl)aniline

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-32752ba40a4a416784d226bcd7e05e8b
出典データセット
uspto-grants-2014_01
特許番号
US08633208B2

関連ノート

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