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Sodium Iodide → 7-[3-[[(2,3-Dihydro-5-methoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one

HRID 374208
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 374208
[CH3:1][O:2][C:3]1[C:12]2[O:11][CH2:10][CH:9]([CH2:13][NH2:14])[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26](=[O:30])[O:27]2)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:12]2[O:11][CH2:10][CH:9]([CH2:13][NH:14][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]4[CH:24]=[CH:25][C:26](=[O:30])[O:27][C:28]=4[CH:29]=3)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1
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Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 189972252,3-Dihydro-5-methoxy-1,4-benzodioxin-2-methanamine

Produkt 1

HCID 197786667-[3-[[(2,3-Dihydro-5-methoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-oneAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,3-Dihydro-5-methoxy-1,4-benzodioxin-2-methanamine (1.29 g, 6.61 mmole), 7-(3-chloropropoxy)coumarin (1.59 g, 6.7 mmole), diisopropylethylamine (2.5 ml, 14.35 mmole) and sodium iodide (4.96 g, 33.1 mmole) were combined in 75 ml of DMF and heated at 80°-100° C. for 3 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 30% ethyl acetate/dichloromethane as eluant. The product-containing fractions (Rf=0.25 on silica gel tlc with 2.5% methanol/dichloromethane) were combined and concentrated in vacuum and the residue (0.68 g) redissolved in dichloromethane and boiled on a hot plate, the dichloromethane gradually being replaced with isopropanol. 2N HCl/isopropanol (4 ml) was added and the title compound was collected by filtration and dried in vacuum at 80° C. The procedure yielded 0.64 g of white solid, monohydrochloride, m.p. 202°-204° C.

Aufarbeitung

  1. temperatureheated at 80°-100° C. for 3 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 30% ethyl acetate/dichloromethane as eluant
  8. concentrationconcentrated in vacuum
  9. dissolutionthe residue (0.68 g) redissolved in dichloromethane
  10. addition2N HCl/isopropanol (4 ml) was added
  11. filtrationthe title compound was collected by filtration
  12. customdried in vacuum at 80° C

Quellen und Nachweise

ORD-Eintrag
ord-f6f22a15ca58484198ab2614ed05fb9d
Quelldatensatz
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05166367

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