Azidotrimethylsilane → HCID 178423708, compound

HRID 1080737Notes

Reaction equation

HRID 1080737 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]#[CH:15])=[CH:4][CH:3]=1.C[Si]([N:20]=[N+:21]=[N-:22])(C)C>>[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]2[N:20]=[N:21][NH:22][CH:15]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 23365411HCID 23365411, compound

Product 1

HCID 178423708HCID 178423708, compoundYield 44%

Procedure

A solution of 2.52 g (13.1 mmol) of 4-methyl-2'-ethynyl-1,1'-biphenyl in 18 mL of trimethylsilyl azide under a nitrogen atmosphere was heated at 120° C. for 72 hours. The volume was reduced by distillation at atmosphere pressure. The residue was dissolved in methylene chloride. The organic layer was washed with water (3×) dried over magnesium sulfate, filtered and evaporated under vacuum to yield 3.1 g of crude product which was purified over silica gel, eluting with hexane/ethyl acetate (3:1) to yield 1.35 g (5.77 mmol, 44%) of the product. FAB-MS: calculated for C15H13N3 235; found 237. 1H NMR (400 MHz, CDCl3): 2.38 (s, 3H), 7.0 (s, 1H), 7.20 (dd, 4H), 7.40 (m, 3H), 7.80 (dd, 1H).

Workup

  1. distillationThe volume was reduced by distillation at atmosphere pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washThe organic layer was washed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto yield 3.1 g of crude product which
  8. customwas purified over silica gel
  9. washeluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-2283e2c370ca4cc7a6210608f1d58342
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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