4-Methyl-3-nitrobenzoyl chloride → 6-(4-Methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

HRID 15025

Reaktionsgleichung

Reaktionsgleichung von HRID 15025
[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].[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>P(Cl)(Cl)(Cl)=O>[CH3:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]2[S:19][C:3]3=[N:4][N:5]=[C:6]([C:7]4[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=4)[N:2]3[N:1]=2)=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]

Komponenten

4

Edukt 2

HCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 178488244HCID 178488244, Verbindung

Produkt 1

HCID 249548716-(4-Methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoleAusbeute 87,9 %

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 (220 mg, 0.78 mmol) and 4-methyl-3-nitrobenzoyl chloride (156 mg, 0.78 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 by aqueous sodium carbonate. The organic layer was dried over sodium sulfate, and concentrated to give 293 mg (85%) of the title compound as solid. 1H NMR (CDCl3): 8.59 (d, J=2.1 Hz, 1H), 8.05-8.01 (dd, J=7.8, 1.8 Hz, 1H), 7.73 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 4.02 (s, 6H), 3.95 (s, 3H), 2.75 (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-321f1925f9ae4c01af76f2f17cfae4fa
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732468B2

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