Triethylamine → 2,2,2-trifluoro-N'-(4-cyanophenyl)ethanehydrazonamide

HRID 584738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584738
C(N(CC)CC)C.Cl.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1)#[N:10].[F:19][C:20]([F:25])([F:24])[C:21](N)=[NH:22]>CO>[F:19][C:20]([F:25])([F:24])[C:21](=[N:18][NH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]#[N:10])=[CH:12][CH:13]=1)[NH2:22]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2776882TrifluoroacetamidineHCID 162129624-Cyanophenylhydrazine Hydrochloride

Produkt 1

HCID 696776302,2,2-trifluoro-N'-(4-cyanophenyl)ethanehydrazonamideAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Triethylamine (1.54 mL, 11 mmol) and then 4-cyanophenylhydrazine hydrochloride (1.71 g, 10 mmol) were added to a solution of trifluoroacetoamidine (1.57 g, 14 mmol) in methanol (10 mL). The mixture was stirred overnight. The solvent was removed under reduced pressure. 20 mL of water and 50 mL of ethyl acetate-tetrahydrofuran (9:1) were added to the residue and the organic layer was separated and the aqueous layer was extracted with 50 mL of ethyl acetate-tetrahydrofuran (9:1). A combined organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was isolated by filtartion, washed with diisopropyl ether-hexane, and dried in vacuo to give 2,2,2-trifluoro-N′-(4-cyanophenyl)ethanehydrazonamide (2.07 g, 90.5% yield).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. addition20 mL of water and 50 mL of ethyl acetate-tetrahydrofuran (9:1) were added to the residue
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with 50 mL of ethyl acetate-tetrahydrofuran (9:1)
  5. washA combined organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was isolated by filtartion
  9. washwashed with diisopropyl ether-hexane
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-63cecc7b19514f71b7f81d0d5cb17a2b
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927230B2

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