Cyclopropanecarbonyl chloride → HCID 45588498, Verbindung

HRID 2045923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045923
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1>N1C=CC=CC=1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:17][C:21]([CH:18]2[CH2:20][CH2:19]2)=[O:22])[CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 8072643-(2-Quinoxalinyl)aniline

Produkt 1

HCID 45588498HCID 45588498, VerbindungAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of (3-quinoxalin-2-ylphenyl)amine (2.21 g, 0.01 mol) in pyridine (10 mL) was cooled to 0° C. and cyclopropanecarbonyl chloride (0.91 mL, 0.01 mol) was added dropwise over 10 min. The reaction mixture was stirred overnight at room temperature, diluted with water (50 mL) and stirred for 30 min. The resulting solid was filtered, dried, and recrystallized from toluene to afford N-[3-(quinoxalin-2-yl)phenyl]cyclopropanecarboxamide (2.0 g, 69% yield). LCMS calculated for C18H15N3O (M+H): 290.34. found 290. 1H-NMR (DMSO-d6, 250 Mhz) δH: 10.45 (1H, br. s), 9.48 (1H, s), 8.52 (1H, s), 8.20-8.05 (2H, m), 8.05-7.80 (4H, m), 7.50 (1H, m), 1.90-1.75 (1H, m), 1.40-1.32 (4H, m).

Aufarbeitung

  1. stirringstirred for 30 min
  2. filtrationThe resulting solid was filtered
  3. customdried
  4. customrecrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-b3046ef601bc4748ae144d97e4ac2e29
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592415B2

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