Triethylamine → 5-([1,1'-Biphenyl]-4-ylcarbonyl)-4,5-dihydropyrrolo[1,2-a]quinoxaline

HRID 440780

Reaktionsgleichung

Reaktionsgleichung von HRID 440780
[CH:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C:4]2=[CH:3][CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:14]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[C:14]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:15]=[CH:16][C:17]([C:20]([N:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]3[CH:1]=[CH:2][CH:3]=[C:4]3[CH2:13]2)=[O:21])=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 118051814,5-Dihydropyrrolo[1,2-a]quinoxaline

Produkt 1

HCID 110681015-([1,1'-Biphenyl]-4-ylcarbonyl)-4,5-dihydropyrrolo[1,2-a]quinoxalineAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 0.5 g of 4,5-dihydropyrrolo[1,2-a]quinoxaline and 0.96 g of 4-biphenylcarbonyl chloride in 50 ml of methylene chloride under argon is added 7.0 ml of triethylamine followed by stirring at room temperature for 16 hours. The reaction mixture is diluted with 50 ml of chloroform and washed with water, 2N HCl, saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and columned on silica gel by elution with 7:1 to 1:1 ethyl acetate:hexane to give 0.87 g of the desired product as a solid. M+H 351.2; M+Na 373.2.

Aufarbeitung

  1. washwashed with water, 2N HCl, saturated NaHCO3 and water
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. washcolumned on silica gel by elution with 7:1 to 1:1 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a39263b5c6eb416c88169a6e46ae651f
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521173

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