3,5-Dichlorobenzoic acid → HCID 178462985, Verbindung

HRID 273118

Reaktionsgleichung

Reaktionsgleichung von HRID 273118
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](O)=O.C(N(CC)CC)C.ClC(OC[CH:24]([CH3:26])C)=O.C[NH:28][C:29](=[S:32])[NH:30][NH2:31]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:28]([CH2:24][CH3:26])[C:29]([SH:32])=[N:30][N:31]=2)[CH:8]=[C:9]([Cl:11])[CH:10]=1

Komponenten

6

Edukt 4

HCID 58113,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 2723853N-Methylhydrazinecarbothioamide

Produkt 1

HCID 178462985HCID 178462985, VerbindungAusbeute 8,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3,5-Dichloro-benzoic acid (382 mg, 2 mmol) was mixed with triethylamine (606 mg, 3 mmol) in THF (6 ml) at 10° C. Then isobutyl chloroformate (300 mg, 2.2 mmol) was added dropwise and stirred for 45 min. To the reaction mixture, 4-methyl-3-thiosemicarbazide (238.4 mg, 2 mmol) was added. After being stirred at room temperature for 10 min, the reaction mixture was heated to 70° C. overnight. Standard work-up. The product was purified by column chromatography with 25˜30% ethyl acetate in hexanes to give 46.4 mg (8.5%) of 5-(3,5-dichloro-phenyl)-4-ethyl-4H-[1,2,4]triazole-3-thiol.

Aufarbeitung

  1. stirringAfter being stirred at room temperature for 10 min
  2. customThe product was purified by column chromatography with 25˜30% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e822db12a34d4ad296bf027c2f54e953
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456200B2

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