Water → 1-Trityl-1H-1,2,4-triazole

HRID 2103972Notes

Reaction equation

HRID 2103972 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

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 (ethyl acetate: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%.

Workup

  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 (ethyl acetate
  8. concentrationThe fraction of the objective was concentrated

Sources & evidence

ORD record
ord-65cf48dfe1664faa8003259f02cd286a
Source dataset
uspto-grants-2009_08
Patent number
US07576198B1

Reaction notes

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