Water → 1-Trityl-1H-1,2,4-triazole

HRID 479437

Reaktionsgleichung

Reaktionsgleichung von HRID 479437
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CCCCCC.CN(C=O)C>[C:8]([N:3]1[CH:7]=[N:6][CH:5]=[N:4]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6456Trityl chlorideHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydride

Produkt 1

HCID 46382511-Trityl-1H-1,2,4-triazoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil, 13.8 g, 345 mmol) was washed with hexane and suspended in DMF (150 ml). At an ice bath temperature, 1,2,4-triazole (total; 20.7 g, 300 mmol) was added thereto in four divisions. After stirring for 30 minutes, to the mixture was added tritylchloride (total; 83.7 g, 300 mmol) in seven divisions and additionally added DMF (50 ml). After stirring for 1.5 hours at room temperature, to the reaction mixture was added water (600 ml). The precipitated crystal was collected by filteration, washed with water, dissolved in CHCl3 (800 ml) and dried. The solvent was evaporated. The obtained residue was chromatographed on silica gel (ethylacetate:CHCl3=1:2, v/v). The fraction of the objective was concentrated to give 1-trityl-1H-1,2,4-triazole (43.9 g). Yield: 47%.

Aufarbeitung

  1. stirringAfter stirring for 1.5 hours at room temperature, to the reaction mixture
  2. customThe precipitated crystal was collected by filteration
  3. washwashed with water
  4. dissolutiondissolved in CHCl3 (800 ml)
  5. customdried
  6. customThe solvent was evaporated
  7. customThe obtained residue was chromatographed on silica gel (ethylacetate
  8. concentrationThe fraction of the objective was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-de4ed7863e41441e877b4780cde5e69b
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645956B1

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