Triethylamine → 2-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazolone

HRID 129164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129164
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]=[CH:11]C(O)=O)=[CH:5][CH:4]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1>C1(C)C=CC=CC=1>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:22](=[O:31])[NH:19][CH:11]=[N:10]2)=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69587423{2-[4-(Trifluoromethyl)phenyl]hydrazinylidene}acetic acid

Produkt 1

HCID 1355070392-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazoloneAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-(trifluoromethyl)phenylhydrazonoacetic acid (6.26 g, 27 mmol) was suspended in 176 ml of toluene, and 4.0 ml of triethylamine (28.7 mmol) and 6.1 ml of diphenylphosphorylazide (28.3 mmol) were added and the resulting mixture was stirred for one hour at 120° C. After cooling, the reaction solution was extracted with 200 ml of an aqueous solution of pottasium hydroxide (10%). The aqueous extract was acidified with concentrated hydrochloric acid to adjust pH to 1, and the crystals thus separated out were washed with water and hexane successively and dried over phosphorus pentoxide to give 4.48 g of 2-(4-trifluoromethylphenyl)-3(2H,4H)-1,2,4-triazolone (72%) as a colorless powder.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe reaction solution was extracted with 200 ml of an aqueous solution of pottasium hydroxide (10%)
  3. extractionThe aqueous extract
  4. customthe crystals thus separated out
  5. washwere washed with water and hexane successively
  6. dry with materialdried over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-aa5cc56ce697452f8e57ae325504ac0f
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466820

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