Dibutyltin oxide → 1-[1,2-diisopropoxyimino-2-(1H-tetrazol-5-yl)ethyl]-1H-1,2,4-triazole

HRID 339428Notes

Reaction equation

HRID 339428 reaction equation
[C:1]([C:3](=[N:15][O:16][CH:17]([CH3:19])[CH3:18])[C:4]([N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)=[N:5][O:6][CH:7]([CH3:9])[CH3:8])#[N:2].C[Si]([N:24]=[N+:25]=[N-:26])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH:7]([O:6][N:5]=[C:4]([N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)[C:3](=[N:15][O:16][CH:17]([CH3:19])[CH3:18])[C:1]1[NH:26][N:25]=[N:24][N:2]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 866815701-(2-cyano-1,2-diisopropoxyiminoethyl)-1H-1,2,4-triazole

Product 1

HCID 1784601781-[1,2-diisopropoxyimino-2-(1H-tetrazol-5-yl)ethyl]-1H-1,2,4-triazoleYield 49.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 5 ml of a toluene solution containing 0.40 g (1.51 mmol) of 1-(2-cyano-1,2-diisopropoxyiminoethyl)-1H-1,2,4-triazole were added 0.35 g (3.03 mmol) of trimethylsilylazide and 0.38 g (1.51 mmol) of di-n-butyltin oxide, followed by stirring for 3 hours under heating and refluxing. The reaction mixture was cooled to room temperature, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/0). The crystal obtained was washed with isopropyl ether to obtain 0.23 g (yield: 47%) of a title compound.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract solution was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elutant:ethyl acetate/hexane=1/0)
  8. customThe crystal obtained
  9. washwas washed with isopropyl ether

Sources & evidence

ORD record
ord-fe00905b85794216a096c58262ac5b79
Source dataset
uspto-grants-2014_11
Patent number
US08895035B2

Reaction notes

Loading…