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

HRID 1674494Notes

Reaction equation

HRID 1674494 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-91485ccadc7847789fa1aa4c0d0830ed
Source dataset
uspto-grants-2011_08
Patent number
US08003638B2

Reaction notes

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