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

HRID 472158

반응식

HRID 472158 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-32752ba40a4a416784d226bcd7e05e8b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633208B2

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