Tributyltin azide → HCID 178439918, compound

HRID 440846Notes

Reaction equation

HRID 440846 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[N:23])=[CH:12][CH:11]=2)[C:7]2[CH:24]=[C:25]([N:29]3C(=O)C4=CC=CC=C4C3=O)[CH:26]=[C:27]([CH3:28])[C:6]=2[N:5]=1)[CH2:2][CH3:3].C([Sn]([N:53]=[N+:54]=[N-:55])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:55]=[N:54][N:53]=3)=[CH:14][CH:15]=2)[C:7]2[CH:24]=[C:25]([NH2:29])[CH:26]=[C:27]([CH3:28])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 54457601HCID 54457601, compound

Product 1

HCID 178439918HCID 178439918, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.75 g (12.5 mMol) of 4'-[(2-n-propyl-4-methyl-6-phthalimido-1H-benzimidazol-1-yl)-methyl]-2-cyanobiphenyl are dissolved in 200 ml of absolute toluene and combined with 20.8 g (62.5 mMol) of tributyl tin azide. The reaction mixture is refluxed for 5 days with stirring. Then the solvent is distilled off, the residue is taken up in saline solution and extracted 3 times with 100 ml of ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down. The residue is chromatographed on silica gel (particle size: 0.032-0.063 mm) using as eluant first methylene chloride and then methylene chloride/ethanol (50:1, 25:1 and 9:1). The uniform fractions are combined and evaporated down. The residue is triturated with ether/petroleum ether (1:1) and suction filtered.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 days
  2. distillationThen the solvent is distilled off
  3. extractionextracted 3 times with 100 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated down
  6. customThe residue is chromatographed on silica gel (particle size: 0.032-0.063 mm)
  7. customevaporated down
  8. customThe residue is triturated with ether/petroleum ether (1:1) and suction
  9. filtrationfiltered

Sources & evidence

ORD record
ord-782c492ed92f4d15a42a2e01b404529b
Source dataset
uspto-grants-1996_05
Patent number
US05521177

Reaction notes

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