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Ammonia → HCID 68584641, Verbindung

HRID 17544
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17544
Cl.C([N:4]=C=NCCCN(C)C)C.[Br:13][C:14]1[C:19]2[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:22][C:18]=2[C:17]([C:27](O)=[O:28])=[CH:16][C:15]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.OC1C2N=NNC=2C=CC=1.N>CN(C)C=O>[Br:13][C:14]1[C:19]2[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:22][C:18]=2[C:17]([C:27]([NH2:4])=[O:28])=[CH:16][C:15]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 685849474-Bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic AcidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 68584641HCID 68584641, VerbindungAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (1.61 g, 8.42 mmol) was added to an N,N-dimethylformamide (80 ml) solution of 4-bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic acid (I-256) (2.62 g, 7.02 mmol) and hydroxybenzotriazole (1.14 g, 8.42 mmol), followed by stirring at room temperature for 1 hour. The reaction liquid was cooled at 0° C., then aqueous 28% ammonia (1.42 ml, 21.1 mmol) was put into it, followed by further stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, then saturated sodium bicarbonate water (200 ml) was added, the product was extracted with ethyl acetate (200 ml×2). The organic layer was washed with saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:2) to obtain the entitled compound (2.59 g, 99%) as a yellow white solid.

Aufarbeitung

  1. customThe reaction liquid
  2. temperaturewas cooled at 0° C.
  3. stirringby further stirring at room temperature for 1 hour
  4. customThe reaction liquid
  5. concentrationwas concentrated under reduced pressure
  6. additionsaturated sodium bicarbonate water (200 ml) was added
  7. extractionthe product was extracted with ethyl acetate (200 ml×2)
  8. washThe organic layer was washed with saturated brine (50 ml)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:2)

Quellen und Nachweise

ORD-Eintrag
ord-eae3def2b7324364bd8d651b14d92b4f
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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