Triethylamine → 10-[4-[[(2-Chlorophenyl)sulfonyl]amino]benzoyl]-10,11-dihydro-5H-pyrrolo(2,1-c][1,4]benzodiazepine

HRID 55219

Reaktionsgleichung

Reaktionsgleichung von HRID 55219
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[NH2:12][C:13]1[CH:34]=[CH:33][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[CH:30]=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:12][C:13]1[CH:34]=[CH:33][C:16]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[CH:30]=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:15][CH:14]=1)(=[O:10])=[O:9]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 1534067710-[4-[[(2-Chlorophenyl)sulfonyl]amino]benzoyl]-10,11-dihydro-5H-pyrrolo(2,1-c][1,4]benzodiazepineAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 0.418 g of 2-chlorobenzenesulfonyl chloride in 5 ml of dichloromethane, cooled to 0° C. is added 0.50 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.346 μl of triethylamine. The mixture is stirred at room temperature overnight and diluted with 50 ml of dichloromethane. The mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3, brine and dried (Na2SO4). The solution is 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 (4) with the solvent ethyl acetate-hexane (1:1) to give a solid. Crystallization from ethyl acetate gives 0.165 g of white crystals, m.p. 206°-210° C.

Aufarbeitung

  1. washThe mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  4. concentrationthe filtrate concentrated to dryness
  5. customThe residue is chromatographed on thick layer silica gel plates (4) with the solvent ethyl acetate-hexane (1:1)
  6. customto give a solid
  7. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-618d9d799dce47758ef2058461c1f7b6
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624923

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