Sodium Iodide → HCID 19778665, Verbindung

HRID 374212

Reaktionsgleichung

Reaktionsgleichung von HRID 374212
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][NH2:12])[O:7][C:6]=2[CH:13]=1.Cl[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25](=[O:29])[O:26]2)=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+].Cl.CC(O)C>CN(C=O)C.CO.C(O)(C)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][NH:12][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[CH:23]=[CH:24][C:25](=[O:29])[O:26][C:27]=4[CH:28]=3)[O:7][C:6]=2[CH:13]=1

Komponenten

9

Edukt 5

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 18923891HCID 18923891, VerbindungHCID 21912024Isopropanol hydrochloride

Produkt 1

HCID 19778665HCID 19778665, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 3776IsopropanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine (3.00 g, 16.6 mmole), 7-(3-chloropropoxy)coumarin (2.95 g, 12.4 mmole), diisopropylethylamine (8.0 ml, 46.0 mmole) and sodium iodide (2.58 g, 17.2 mmole) were combined in 150 ml of DMF and heated at 80°-100° C. for 2 days under a nitrogen atmosphere. The solvent was then removed and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on silica gel using first dichloromethane and then 0.25% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the pure free base (1.0 g, an additional 2.0 g were obtained of lower purity) redissolved in methanol and boiled on a hot plate, the methanol gradually being replaced with isopropanol. 4N HCl/IPA was added and the title compound was collected by filtration and dried in vacuum at 80° C. The procedure yielded 0.76 g of beige solid, monohydrochloride, m.p. 252° C. (d).

Aufarbeitung

  1. temperatureheated at 80°-100° C. for 2 days under a nitrogen atmosphere
  2. customThe solvent was then removed
  3. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on silica gel using first dichloromethane
  8. concentrationconcentrated in vacuum
  9. customthe pure free base (1.0 g, an additional 2.0 g were obtained of lower purity)
  10. filtrationthe title compound was collected by filtration
  11. customdried in vacuum at 80° C

Quellen und Nachweise

ORD-Eintrag
ord-37ea97c2bcb44e0db0b441e64c640a41
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166367

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