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Sodium Hydroxide → HCID 178432262, Verbindung

HRID 74486
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74486
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20](CC2C=CC(OC)=CC=2)[C:21]([Br:25])=[C:22]([Br:24])[CH:23]=1)=[O:18].[OH-].[Na+]>C(OCC)(=O)C.S(=O)(=O)(O)O>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[NH:20][C:21]([Br:25])=[C:22]([Br:24])[CH:23]=1)=[O:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 178490813HCID 178490813, Verbindung

Produkt 1

HCID 178432262HCID 178432262, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86628183Ethyl acetate sulfuric acidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

[5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[4,5-dibromo-1-(4-methoxy-benzyl)-1H-pyrrol-2-yl]-methanone (317 mg) was dissolved in ethyl acetate/sulfuric acid (4/1; 5 ml). This was stirred at 80° C. for four hours. The pH of the reaction mixture was adjusted to 11 (basic) using an aqueous solution of 5 M sodium hydroxide while cooling it on ice. The reaction mixture was extracted with ethyl acetate/tetrahydrofuran (THF) (10 ml). The organic layer was washed with an aqueous solution saturated with sodium chloride (5 ml), and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol). Thus, a brown solid was obtained (135 mg, 54%).

Aufarbeitung

  1. temperaturewhile cooling it on ice
  2. extractionThe reaction mixture was extracted with ethyl acetate/tetrahydrofuran (THF) (10 ml)
  3. washThe organic layer was washed with an aqueous solution saturated with sodium chloride (5 ml)
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol)
  6. customThus, a brown solid was obtained (135 mg, 54%)

Quellen und Nachweise

ORD-Eintrag
ord-6ddb47c5946b44fa8a1be4bbc6c1f35e
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829199B2

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