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Water → HCID 54023400, Verbindung

HRID 2211292
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2211292
[CH2:1]([S:3][C:4]1[NH:5][C:6]2[C:7](=[C:9]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:11]=2[CH3:12])[N:8]=1)[CH3:2].[H-].[Na+].[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)#[N:20].O>CN(C=O)C>[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[CH:29][C:30]([CH2:33][N:8]2[C:7]3=[C:9]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:11]([CH3:12])=[C:6]3[N:5]=[C:4]2[S:3][CH2:1][CH3:2])=[CH:31][CH:32]=1)#[N:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 178418569HCID 178418569, Verbindung

Produkt 1

HCID 54023400HCID 54023400, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

To a solution of methyl 2-ethylthio-4-methylthieno[3,4-d]imidazole-6-carboxylate (5.7 g) in DMF (30 ml) was added sodium hydride (60% oil, 0.98 g) under ice-cooling. After stirring the reaction mixture for 20 minutes, to the mixture was added dropwise a solution of (2'-cyanobiphenyl-4-yl)methyl bromide (7.25 g) in DMF (20 ml), followed by stirring for one hour at room temperature. To the reaction mixture was added water, which was extracted with ethyl acetate. The extract was washed with water and dried, then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography to give crystals. Recrystallization from ethyl acetate - hexane afforded pale yellow prisms (7.6 g, 77%), m.p. 149°-151° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring for one hour at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. customto give crystals
  9. customRecrystallization from ethyl acetate - hexane afforded pale yellow prisms (7.6 g, 77%), m.p. 149°-151° C.

Quellen und Nachweise

ORD-Eintrag
ord-10fcaf7ab5ed444784ac0f8a15189fbc
Quelldatensatz
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05463073

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