5-Benzimidazolecarboxylic acid → 6-(1H-Benzo[d]imidazol-6-yl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

HRID 15027

反応式

HRID 15027 の反応式
[NH2:1][N:2]1[C:6]([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=2)=[N:5][N:4]=[C:3]1[SH:19].[N:20]1[C:24]2[CH:25]=[CH:26][C:27]([C:29](O)=O)=[CH:28][C:23]=2[NH:22][CH:21]=1>P(Cl)(Cl)(Cl)=O>[NH:22]1[C:23]2[CH:28]=[C:27]([C:29]3[S:19][C:3]4=[N:4][N:5]=[C:6]([C:7]5[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=5)[N:2]4[N:1]=3)[CH:26]=[CH:25][C:24]=2[N:20]=[CH:21]1

参加物

4

反応物 2

HCID 4594565-Benzimidazolecarboxylic acidHCID 178488244HCID 178488244、化合物

生成物 1

HCID 249548726-(1H-Benzo[d]imidazol-6-yl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole収率 17.5%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

A mixture of 4-amino-3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole (80 mg, 0.28 mmol) and 3H-benzo[d]imidazole-5-carboxylic acid (46 mg, 0.28 mmol) in phosphoryl chloride (2 mL) was refluxed for 3 h. The solvent was evaporated and the residue was dissolved in dichloromethane (20 mL). It was neutralized with aqueous sodium carbonate. The organic layer was dried over sodium sulfate, concentrated to give 20 mg (17%) of the title compound as a solid. 1H NMR (CD3OD): 8.55 (s, 1H), 8.35 (s, 1H), 8.01-7.85 (m, 2H), 7.72 (s, 1H), 3.99 (s, 6H), 3.87 (s, 3H).

後処理

  1. temperaturewas refluxed for 3 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane (20 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-33ed9116bcc6491594f2303dbec72685
出典データセット
uspto-grants-2010_06
特許番号
US07732468B2

関連ノート

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