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Potassium Carbonate → HCID 22227859, Verbindung

HRID 1744577
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1744577
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10]([OH:12])=O)[CH:6]=[N:5]1.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[C:18]([CH:21]=1)[C:19]#[N:20].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:19]([C:18]1[CH:21]=[C:14]([NH:13][C:10]([C:7]2[CH:6]=[N:5][N:4]([CH2:3][CH2:2][OH:1])[C:8]=2[CH3:9])=[O:12])[CH:15]=[CH:16][C:17]=1[O:22][CH2:23][C:24]([CH3:26])([CH3:25])[CH3:27])#[N:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 167776201-(2-hydroxyethyl)-5-methyl-1H-pyrazole-4-carboxylic acidHCID 178227345-Amino-2-neopentyloxybenzonitrile

Produkt 1

HCID 22227859
HCID 22227859, Verbindung
Ausbeute 30,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(2-Hydroxyethyl)-5-methylpyrazole-4-carboxylic acid (1.7 g), 5-amino-2-neopentyloxybenzonitrile (2.1 g), 1-hydroxybenzotriazole (1.6 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (2.3 g) were added to dimethylformamide (20 ml) and the mixture was stirred at room temperature for 5 h. The reaction mixture was treated with aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=100:1). Diisopropyl ether was added to the obtained oily substance to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether to give the title compound (1.1 g), melting point: 98–100° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=100:1)
  6. additionDiisopropyl ether was added to the obtained oily substance
  7. customcrystallization
  8. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-93a27f8fd8844ce5bcbd5977e4cf384e
Quelldatensatz
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07015218B1

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