Dibutyltin oxide → HCID 178526720, compound

HRID 856688Notes

Reaction equation

HRID 856688 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]#[N:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].C[Si]([N:18]=[N+:19]=[N-:20])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][C:12]2[NH:20][N:19]=[N:18][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 13068864[(4-Nitrophenyl)sulfanyl]acetonitrile

Product 1

HCID 178526720HCID 178526720, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-[(4-nitrophenyl)sulfanyl]acetonitrile (6.8 g) was added toluene (70 ml), and to this solution was added trimethylsilylazide (8.1 g) and then, dibutyl tin oxide (VI) (0.87 g), and the mixture was heated to reflux for 6 hours. After allowing the mixture to be cooled to room temperature, the solvent was removed under reduced pressure, and azeotropically distilled with methanol. To the obtained residue was added 10% aqueous solution (50 ml) of sodium carbonate, and the mixture was washed with ethyl acetate. The pH was adjusted to about pH 3 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was washed with hexane/ethyl acetate to give 5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole (6.7 g).

Workup

  1. temperatureto reflux for 6 hours
  2. customthe solvent was removed under reduced pressure
  3. distillationazeotropically distilled with methanol
  4. additionTo the obtained residue was added 10% aqueous solution (50 ml) of sodium carbonate
  5. washthe mixture was washed with ethyl acetate
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed under reduced pressure
  10. washthe residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-1e0bb7f84bc3459c9092e1f4c584320e
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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