1H-1,2,4-Triazole → 3-chloro-N-{4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl}-4-(1H-1,2,4-triazol-1-ylmethyl)thiophene-2-carboxamide

HRID 370111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370111
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:35])[C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25]([C:27]2[S:28][CH:29]=[C:30]([CH2:33]Cl)[C:31]=2[Cl:32])=[O:26])=[CH:11][CH:10]=1>CN(C=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:35])[C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25]([C:27]2[S:28][CH:29]=[C:30]([CH2:33][N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[C:31]=2[Cl:32])=[O:26])=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 18376557N-(4-chlorophenyl)-2-[((4-(chloromethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

Produkt 1

HCID 183769763-chloro-N-{4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl}-4-(1H-1,2,4-triazol-1-ylmethyl)thiophene-2-carboxamideAusbeute 102,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 1,2,4-triazole (0.40 g, 5.7 mmol) in DMF (10 mL) was added NaH (60% dispersion in mineral oil, 0.23 g, 5.7 mmol) and the mixture stirred at ambient temperature. After 10 min, N-(4-chlorophenyl)-2-[((4-(chloromethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide (0.90 g, 1.9 mmol) in DMF (5 mL) was added and stirring continued. After 18 hours, the mixture was poured onto water and extracted with methylene chloride. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 0.99 g (77% yield) of N-(4-chlorophenyl)-2-[((3-chloro-4-((1,2,4-triazol-1-yl)methyl)thiophen-2-yl)carbonyl)amino]-5-chlorobenzamide; as a white solid; NMR (DMSO-d6 /TFA) 11.2 (s, 1), 10.7 (s, 1), 9.3 (s, 1), 8.5 (s, 1), 8.3 (d, 1), 8.0 (s, 1), 7.9 (d, 1), 7.7 (d, 2), 7.6 (dd, 1), 7.4 (d, 2), 5.5 (s, 2) ppm.

Aufarbeitung

  1. stirringstirring
  2. waitAfter 18 hours
  3. additionthe mixture was poured onto water
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-910a859d305a4ef59f9339b657a2930f
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140351

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