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Dimethylformamide → 1-[2-(4-Chlorophenyl)-2-cyano-4-(2-thienyl)butyl]-1,2,4-triazole

HRID 2255387
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Reaktionsgleichung

Reaktionsgleichung von HRID 2255387
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[C:11]#[N:12])=[CH:6][CH:5]=1.CN(C=O)C.Cl.Cl[CH2:27][N:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CCCCCC.CCOCC.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:11]#[N:12])([CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[CH2:27][N:28]2[CH:32]=[N:31][CH:30]=[N:29]2)=[CH:8][CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13268168HCID 13268168, VerbindungHCID 197380262-(4-Chlorophenyl)-4-(2-thienyl)butyronitrile

Produkt 1

HCID 197380521-[2-(4-Chlorophenyl)-2-cyano-4-(2-thienyl)butyl]-1,2,4-triazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a flask under a nitrogen atmosphere was added, with stirring, 1.5 g. (0.036 mole) of 60% sodium hydride, washed twice with hexane to remove the original mineral oil, in 30 ml. of dry DMF. To this slurry at room temperature was added 3.36 g. (12.8 mmoles) of 2-(4-chlorophenyl)-4-(2-thienyl)butyronitrile in 30 ml. of DMF over 10 minutes. After stirring for 30 minutes, 2.15 g. (14.08 mmoles) of 1-(chloromethyl)-1,2,4-triazole hydrochloride was added in two portions and stirred for another 60 minutes. Water, 20 ml., was then added followed by 100 ml. of ether. The ether layer was washed twice with 50 ml. portions of water and the water washes further extracted with 50 ml. of ether. The combined ether extracts were chromatographed on 50 g. of silica gel. The product was eluted with ethyl acetate yielding 1.17 g. of product as a thick brown oil.

Aufarbeitung

  1. additionTo a flask under a nitrogen atmosphere was added
  2. customto remove the original mineral oil
  3. additionTo this slurry at room temperature was added 3.36 g
  4. stirringAfter stirring for 30 minutes
  5. stirringstirred for another 60 minutes
  6. addition, was then added
  7. washThe ether layer was washed twice with 50 ml
  8. extractionfurther extracted with 50 ml
  9. customThe combined ether extracts were chromatographed on 50 g
  10. washThe product was eluted with ethyl acetate yielding 1.17 g

Quellen und Nachweise

ORD-Eintrag
ord-69469907670e4ad4979462923c915ff6
Quelldatensatz
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05240925

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