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

HRID 1674494ノート

反応式

HRID 1674494 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-91485ccadc7847789fa1aa4c0d0830ed
出典データセット
uspto-grants-2011_08
特許番号
US08003638B2

反応ノート

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