1H-苯并咪唑-5-羧酸 → 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

反应方程式

HRID 15027 反应方程式
[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

参与物

4

反应物 2

HCID 4594561H-苯并咪唑-5-羧酸HCID 178488244HCID 178488244，化合物

产物 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收率 17.5%

试剂、催化剂与溶剂 1

HCID 24813三氯氧磷溶剂

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-33ed9116bcc6491594f2303dbec72685
来源数据集
uspto-grants-2010_06
专利号
US07732468B2

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