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Potassium Iodide → HCID 14722394, Verbindung

HRID 1031721
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1031721
[NH2:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:5]=2[O:4][CH:3]=1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu].C(OCC)(=O)C.O>[CH3:17][S:14]([NH:13][C:11]1[C:10]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:9][C:6]2[C:7](=[O:8])[C:2]([NH:1][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:3][O:4][C:5]=2[CH:12]=1)(=[O:15])=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 4875Potassium IodideHCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 10783765HCID 10783765, Verbindung

Produkt 1

HCID 14722394HCID 14722394, VerbindungAusbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23978
Copper
Katalysator
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.46 g of 3-amino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one was dissolved in 35 ml of N,N-dimethylformamide. Thereto were added 7 ml of bromobenzene, 1.66 g of potassium iodide, 1.38 g of potassium carbonate and 0.64 g of a copper powder. The mixture was refluxed for 6 hours. The reaction mixture was introduced into a mixture consisting of 300 ml of water and 200 ml of ethyl acetate. The insolubles were removed by filtration, and the filtrate was adjusted to pH 4 with 4N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 20:1 mixture of toluene and ethyl acetate) and then recrystallized from acetonitrile to obtain 430 mg (yield: 10.2%) of 7-methylsulfonylamino-3-phenylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 212°-213° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 6 hours
  2. additionThe reaction mixture was introduced into a mixture
  3. customThe insolubles were removed by filtration
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by a column chromatography (eluant
  9. additiona 20:1 mixture of toluene and ethyl acetate) and
  10. customthen recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-4a6cba48849c4b749532dcac4aa33dc9
Quelldatensatz
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04954518

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