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

HRID 472158

Reaktionsgleichung

Reaktionsgleichung von HRID 472158
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 672049713-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamideAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-32752ba40a4a416784d226bcd7e05e8b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633208B2

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