Dibutyltin oxide → HCID 178497694, compound

HRID 1975273Notes

Reaction equation

HRID 1975273 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2].C([Sn](=O)CCCC)CCC.C[Si]([N:27]=[N+:28]=[N-:29])(C)C>C1(C)C=CC=CC=1>[CH3:9][O:8][C:6]([C:5]1[CH:4]=[C:3]([C:1]2[NH:29][N:28]=[N:27][N:2]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 83554Benzoic acid, 3-cyano-, methyl ester

Product 1

HCID 178497694HCID 178497694, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 3-cyanobenzoate (320 mg, 1.98 mmol), dibutyltin oxide (49.7 mg, 0.20 mmol) and trimethylsilyl azide (0.54 mL, 3.96 mmol) in toluene (4.0 mL) was heated at reflux for 24 hours. The solvent was removed under reduced pressure and chased with methanol (1-2 mL). The residue obtained was flash chromatographed on silica gel eluting with acetic acid and methanol in methylene chloride to give the title compound (395.7 mg). 1H NMR (DMSO-d6, 300 MHz) δ3.0-4.5 (br, 1H), 3.92 (s, 3H), 7.75 (t, J=8 Hz, 1H), 8.11 (d, J=8 Hz, 1H), 8.32 (d, J=8 Hz, 1H), 8.54 (s, 1H). MS (DCl/NH3) m/e 205 (M+H)+, 222 (M+H+NH3)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was removed under reduced pressure and chased with methanol (1-2 mL)
  4. customThe residue obtained
  5. customchromatographed on silica gel eluting with acetic acid and methanol in methylene chloride

Sources & evidence

ORD record
ord-50eb2c51a8244677aa6d68895142a802
Source dataset
uspto-grants-1994_02
Patent number
US05284954

Reaction notes

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