Trichloroacetyl chloride → (4-Trichloroacetoxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile

HRID 1018887

Reaktionsgleichung

Reaktionsgleichung von HRID 1018887
[OH:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:5]=[CH:4]1.[Cl:18][C:19]([Cl:24])([Cl:23])[C:20](Cl)=[O:21].C(N(CC)CC)C>O1CCCC1>[Cl:18][C:19]([Cl:24])([Cl:23])[C:20]([O:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]#[N:11])[CH:5]=[CH:4]1)=[O:21]

Komponenten

5

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 3468332-(4-(Hydroxyimino)cyclohexa-2,5-dien-1-ylidene)-2-phenylacetonitrile

Produkt 1

HCID 18398556(4-Trichloroacetoxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

8 g (36 mmol) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile, prepared as described in example 1.1, are dissolved in 90 ml of tetrahydrofuran (THF) and cooled in an ice bath. After adding 7.2 g (39 mmol) of trichloroacetyl chloride to the solution, 5.4 g (54 mmol) of triethylamine are added dropwise, keeping the temperature below 5° C. While the reaction mixture is stirred at 5° C. for 50 min, a precipitate is formed. The precipitate is filtered off and washed with THF. The filtrate is concentrated by a rotary evaporator. The residue is diluted with 2-propanol (2-PrOH) and stirred at room temperature overnight. After cooling the mixture in an ice bath, the solid is isolated by filtration and washed with 2-PrOH. The product is obtained in the form of an orange solid,mp 147-148° C.(Dec). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 6.97 (dd, 1H), 7.30 (dd, 1H), 7.38 (dd, 1H), 7.52 (s, 5H), 7.65 (dd, 1H). 1H-NMR reveals the presence of a single isomer.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 5° C
  4. customa precipitate is formed
  5. filtrationThe precipitate is filtered off
  6. washwashed with THF
  7. concentrationThe filtrate is concentrated by a rotary evaporator
  8. additionThe residue is diluted with 2-propanol (2-PrOH)
  9. stirringstirred at room temperature overnight
  10. temperatureAfter cooling the mixture in an ice bath
  11. customthe solid is isolated by filtration
  12. washwashed with 2-PrOH
  13. customThe product is obtained in the form of an orange solid,mp 147-148° C.(Dec)

Quellen und Nachweise

ORD-Eintrag
ord-1e3a41df64eb43acb3744624a185062f
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06485886B1

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