2-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide → HCID 178425397, Verbindung

HRID 1088291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088291
C[O-].[Na+].[NH2:4][C:5](=[S:26])[NH:6][NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH3:23])[C:17]=1[Cl:24]>CO>[Cl:24][C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]1[NH:4][C:5](=[S:26])[NH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 98641092-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazideHCID 10942334Sodium Methoxide2×

Produkt 1

HCID 178425397HCID 178425397, VerbindungAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium methoxide (734.0 mg, 13.59 mmol) is added to a solution of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)-hydrazide (1.466 g, 3.96 mmol) in 60 ml of methanol and the mixture is heated at reflux overnight, under a nitrogen atmosphere. An additional amount of sodium methoxide (702.0 mg, 13.00 mmol) is added and heating at reflux is continued overnight. The volatiles are removed in vacuo and the residue dissolved in water. The aqueous solution is acidified to pH 4-5 with 10% hydrochloric acid. The resultant white solid is collected, dissolved in tetrahydrofuran and chromatographed, eluting with hexane:ethyl acetate (1:2) to give 599.2 mg (43%) of 5-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, mp 300°-305° C.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight, under a nitrogen atmosphere
  3. temperatureheating
  4. temperatureat reflux
  5. customThe volatiles are removed in vacuo
  6. dissolutionthe residue dissolved in water
  7. customThe resultant white solid is collected
  8. dissolutiondissolved in tetrahydrofuran
  9. customchromatographed
  10. washeluting with hexane:ethyl acetate (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-8ec72fd6aab54148aab4f2cd1209ec72
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04962119

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