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

Reaktionsgleichung

Reaktionsgleichung von HRID 15027
[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

Komponenten

4

Edukt 2

HCID 4594565-Benzimidazolecarboxylic acidHCID 178488244HCID 178488244, Verbindung

Produkt 1

HCID 249548726-(1H-Benzo[d]imidazol-6-yl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoleAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-33ed9116bcc6491594f2303dbec72685
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732468B2

Verknüpfte Notizen

Wird geladen…