Hydrochloric Acid → HCID 67790043, Verbindung

HRID 486616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486616
ClC1C=CC(C(NN)=O)=CC=1.C(N=C=O)C.[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([NH:24][NH:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])=O)=[CH:20][CH:19]=1.NNC(N)=O.Cl>O1CCCC1.[OH-].[Na+]>[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([CH:22]2[N:28]([CH2:29][CH3:30])[C:26](=[O:27])[N:25]=[N:24]2)=[CH:20][CH:19]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 5196SemicarbazideHCID 8022Ethyl isocyanateHCID 108164-ChlorobenzohydrazideHCID 13864336HCID 13864336, Verbindung

Produkt 1

HCID 67790043HCID 67790043, VerbindungAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a suspension of 4-chlorobenzhydrazide (98.5 g, 0.05 mole) in tetrahydrofuran (100 ml) at room temperature ethylisocyanate (4.2 g, 0.05 mole) was added slowly with magnetic stirring. The reaction was slightly exothermic and the reaction mixture turned to a thick paste. Stirring was continued an additional 30 min after which the solid was collected by suction-filtration and washed with a small amount of tetrahydrofuran and dried to provide 11.6 g (96.6% yield), of 1-(4chlorobenzoyl)-4-ethyl semicarbazide as a white solid., m.p.=242°-243° C. The above semicarbazide (10 g, 0.0414 mole) was dissolved in 1N sodium hydroxide solution (100 ml) and was refluxed with stirring for 16 hr. The solution was cooled down to about 10° C. by an ice bath and was neutralized by conc. hydrogen chloride until pH 2. The resultant white solid was collected by suction-filtration and washed with water to give 8.65 g (93.5% yield) of 3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one as a white solid. m.p.=190°-197° C. A proton NMR spectrum was consistent with the desired structure.

Aufarbeitung

  1. additionwas added slowly with magnetic stirring
  2. filtrationafter which the solid was collected by suction-filtration
  3. washwashed with a small amount of tetrahydrofuran
  4. customdried
  5. customto provide 11.6 g (96.6% yield)
  6. temperaturewas refluxed
  7. stirringwith stirring for 16 hr
  8. filtrationThe resultant white solid was collected by suction-filtration
  9. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-9777d81fe0cc4a07bab575a85355f8f1
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292762

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