2-Methyl-5-quinolinecarboxylic acid → 4-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazole-3-thiol

HRID 1674494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674494
OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:23][C:24]1[CH:33]=[CH:32][C:31]2[C:30]([C:34](O)=O)=[CH:29][CH:28]=[CH:27][C:26]=2[N:25]=1.[CH3:37][NH:38][C:39](=[S:42])[NH:40][NH2:41]>CN(C)C=O.C(N(CC)CC)C>[CH3:37][N:38]1[C:34]([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:31]=2[CH:32]=[CH:33][C:24]([CH3:23])=[N:25]3)=[N:41][NH:40][C:39]1=[S:42]

Komponenten

7

Edukt 4

HCID 3199762-Methyl-5-quinolinecarboxylic acidHCID 2723853N-MethylhydrazinecarbothioamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 446275704-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazole-3-thiol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Hydroxybenzotriazole (7.8 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11 g) and triethylamine were successively added to a stirred solution of 2-methyl-5-quinolinecarboxylic acid (10g) and 4-methyl-3-thiosemicarbazide (6.1 g) in dimethylformamide (200 ml), at 0° C. Following the addiction the reaction mixture was allowed to reach room temperature, the stirred continued over night and then the solvent was evaporated under reduced pressure. The residue was treated with an aqueous sodium hydroxide solution (500 ml, 0.5N) and the mixture was stirred at 80° C. for 3 h, after which time the mixture was cooled to room temperature and the pH adjusted to pH 6 using a aqueous hydrochloridric acid solution (2M) and the resulting precipitatye was filtered and dried in vacuo to give the title compound (11 g) as an off-white solid.

Aufarbeitung

  1. customto reach room temperature
  2. waitthe stirred continued over night
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe residue was treated with an aqueous sodium hydroxide solution (500 ml, 0.5N)
  5. temperatureafter which time the mixture was cooled to room temperature
  6. filtrationthe resulting precipitatye was filtered
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-91485ccadc7847789fa1aa4c0d0830ed
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003638B2

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