1,1'-Thiocarbonyldiimidazole → 1,2,3,4-Tetrahydro-2-(imidazol-1-yl)thiocarbonyl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

HRID 988315

Reaktionsgleichung

Reaktionsgleichung von HRID 988315
[C:1](N1C=CN=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2].[CH2:13]1[O:21][C:20]2[CH:19]=[CH:18][C:17]([CH:22]3[C:26]4[NH:27][C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=5[C:34](=[O:35])[C:25]=4[CH2:24][NH:23]3)=[CH:16][C:15]=2[O:14]1>CN(C=O)C.O>[N:3]1([C:1]([N:23]2[CH2:24][C:25]3[C:34](=[O:35])[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[NH:27][C:26]=3[CH:22]2[C:17]2[CH:18]=[CH:19][C:20]3[O:21][CH2:13][O:14][C:15]=3[CH:16]=2)=[S:2])[CH:7]=[CH:6][N:5]=[CH:4]1

Komponenten

5

Edukt 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 108921213-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-one

Produkt 1

HCID 129930301,2,3,4-Tetrahydro-2-(imidazol-1-yl)thiocarbonyl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 1,1′-thiocarbonyldiimidazole (0.192 g, 1.08 mmol) in DMF (5 mL, anhydrous) at 0° C. was added 1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one (0.30 g, 0.98 mmol) (prepared as in Example 5). The mixture warmed to room temperature and stirred for 20 h. The solution was diluted with water and extracted into ethyl acetate. The organic layers were combined and washed with aq. NaHCO3 and brine, dried with MgSO4 and concentrated in vacuo, to yield the product as a light tan solid.

Aufarbeitung

  1. extractionextracted into ethyl acetate
  2. washwashed with aq. NaHCO3 and brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f60f258160444f289de438e0f3e41d43
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635638B2

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