Dibutyltin oxide → HCID 178423709, compound

HRID 1975271Notes

Reaction equation

HRID 1975271 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]#[N:15])=[CH:4][CH:3]=1.C[Si]([N:20]=[N+:21]=[N-:22])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[NH:22][N:21]=[N:20][N:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 178423709HCID 178423709, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4-methyl-2'-cyanobiphenyl (53 mg, 0.274 mmol) dissolved in toluene (0.5 mL) was added trimethylsilyl azide (100 μL, 0.73 mmol) and dibutyltin oxide (74 mg, 0.300 mmol). The reaction mixture was heated at ~105° C. for 91 hours, cooled to ambient temperature, concentrated under reduced pressure and flash chromatographed on silica gel eluting with methanol in methylene chloride to give the title compound (61.2 mg). The 300 MHz 1H NMR spectrum was found to be consistent with the desired product.

Workup

  1. temperatureThe reaction mixture was heated at ~105° C. for 91 hours
  2. concentrationconcentrated under reduced pressure and flash
  3. customchromatographed on silica gel eluting with methanol in methylene chloride

Sources & evidence

ORD record
ord-18718448bfe74114a16c51cbc2653f85
Source dataset
uspto-grants-1994_02
Patent number
US05284954

Reaction notes

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