Lithium iodide → HCID 20135083, Verbindung

HRID 580408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580408
[I-].[Li+].COC([C:7]1([CH2:31][CH:32]=[CH2:33])[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][C:11]2[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=[CH:25][C:10]=2[NH:9][C:8]1=[O:30])=O>N1C=CC=CC=1.O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:13]1[CH2:12][C:11]2[C:22]([C:26]([F:27])([F:28])[F:29])=[CH:23][CH:24]=[CH:25][C:10]=2[NH:9][C:8](=[O:30])[CH:7]1[CH2:31][CH:32]=[CH2:33]

Komponenten

5

Edukt 2

HCID 66321Lithium iodideHCID 20135070HCID 20135070, Verbindung

Produkt 1

HCID 20135083HCID 20135083, VerbindungAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterKatalysatorHCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

Lithium iodide (11.98 g; 89.44 mmole) was added to 1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-3-(2-propenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one (9.69 g; 22.36 mmole) in pyridine (40 ml) and water (a few drops). The mixture was refluxed with stirring for 11 hours. The pyridine was vacuum distilled off and the residue was dissolved into methanol and washed with 1N hydrochloric acid (three times), and saturated sodium chloride, and dried (magnesium sulfate). The concentrated residue was black indicating some decomposition occurred. The 9.67 g of this black residue was flash chromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 1:1-hexane/ethyl acetate). Appropriate fractions were combined and concentrated giving 5.87 g of the title compound as a solid.

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. distillationdistilled off
  3. dissolutionthe residue was dissolved into methanol
  4. washwashed with 1N hydrochloric acid (three times), and saturated sodium chloride
  5. dry with materialdried (magnesium sulfate)
  6. customchromatographed (silica gel/3:1-hexane:ethyl acetate, followed by 1:1-hexane/ethyl acetate)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-23cc770041854ba6ae44e2db714a5176
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04752645

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