Triethylamine → N-[4-(Pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]-2,3-dichlorobenzamide

HRID 3579

Reaktionsgleichung

Reaktionsgleichung von HRID 3579
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]3[CH:18]=[CH:19][CH:20]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:30][C:31]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](Cl)=[O:34]>ClCCl>[CH:18]1[N:11]2[C:12]3[C:17]([N:8]([C:6]([C:5]4[CH:4]=[CH:3][C:2]([NH:1][C:33](=[O:34])[C:32]5[CH:36]=[CH:37][CH:38]=[C:39]([Cl:40])[C:31]=5[Cl:30])=[CH:22][CH:21]=4)=[O:7])[CH2:9][C:10]2=[CH:20][CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 179442,3-Dichlorobenzoyl chloride2×HCID 218370054,5-Dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline

Produkt 1

HCID 21837108N-[4-(Pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]-2,3-dichlorobenzamideAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

As described for Example 157, 0.47 g of 4,5-dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline, 346 μl of triethylamine and 5 ml of dichloromethane are chilled (ice bath) and 0.415 g of 2,3-dichlorobenzoyl chloride in 2 ml of dichloromethane added. After stirring overnight, an additional 346 μl of triethylamine is added and an additional 0.415 g of 2,3-dichlorobenzoyl chloride added. The mixture is stirred for 2 hours, diluted with 50 ml of dichloromethane and the solution washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as solvent to give 0.100 g of white solid, m.p. 230°-240° C.

Aufarbeitung

  1. additionadded
  2. stirringThe mixture is stirred for 2 hours
  3. washthe solution washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3 and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered through a thin pad of hydrous magnesium silicate
  6. concentrationthe filtrate concentrated to dryness
  7. customThe residue is chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as solvent

Quellen und Nachweise

ORD-Eintrag
ord-19075005e7214f38bc08e67939d9a779
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

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