Trityl chloride → 3-nitro-1-(triphenylmethyl)-1H-1,2,4-triazole

HRID 606464Notes

Reaction equation

HRID 606464 reaction equation
[N+:1]([C:4]1[N:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[C:9](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[N+:1]([C:4]1[N:8]=[CH:7][N:6]([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 178526901HCID 178526901, compound

Product 1

HCID 667692413-nitro-1-(triphenylmethyl)-1H-1,2,4-triazoleYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-nitro-1H-1,2,4-triazole (1.00 g, 8.77 mmol), trityl chloride (4.89 g, 17.5 mmol) and diisopropylethylamine (3.05 mL, 17.5 mmol) in THF (50 mL) was stirred at room temperature for 15 hr. The mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (15-30% ethyl acetate/hexane) to give the title compound as a white powder (2.90 g, 93%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (15-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6abbfed538404c63914fc3d8eca261fc
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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