Sodium hydride → 2-cyano-3-hydroxy-N-(4-trifluoromethylphenyl)-hexa-2,5-dienamide

HRID 1033036

Reaktionsgleichung

Reaktionsgleichung von HRID 1033036
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]([NH:7][C:8](=[O:12])[CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[H-].[Na+].[C:19](Cl)(=[O:23])[CH2:20][CH:21]=[CH2:22]>O1CCCC1>[C:10]([C:9](=[C:19]([OH:23])[CH2:20][CH:21]=[CH2:22])[C:8]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:15])([F:16])[F:1])=[CH:14][CH:13]=1)=[O:12])#[N:11]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 38238032-Cyano-N-[4-(trifluoromethyl)phenyl]acetamideHCID 10975427But-3-enoyl Chloride

Produkt 1

HCID 677890152-cyano-3-hydroxy-N-(4-trifluoromethylphenyl)-hexa-2,5-dienamideAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6.0 g (0.026 mole) of 4'-trifluoromethyl-cyanoacetanilide in 200 ml of dry tetrahydrofuran were stirred under nitrogen at room temperature and were treated with 1.95 g (0.065 mole) of sodium hydride 80% oil dispersion. The mixture was stirred for a further 30 minutes at room temperature and cooled to -50° C. before the dropwise addition of 3.3 g (0.033 mole) of 3-butenoyl chloride prepared as described in J. Chem. Soc. (1948), p. 661. The mixture was stirred at -50° C. for 2 hours, then was poured onto dilute hydrochloric acid/ice and filtered. The solid was chromatographed over silica gel eluting with dichloromethane to give 2.4 g (31%) of the title compound as colorless crystals and 3 g of starting material were recovered.

Aufarbeitung

  1. customprepared
  2. stirringThe mixture was stirred at -50° C. for 2 hours
  3. filtrationfiltered
  4. customThe solid was chromatographed over silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-ae91e35cfcff40ed9346a51457c95d8c
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05308865

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