Tributyltin azide → HCID 178493528, compound

HRID 2380466Notes

Reaction equation

HRID 2380466 reaction equation
[C:1]([CH:3]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:4][C:5]([NH:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=1[O:18][CH3:19])=[O:6])#[N:2].C([Sn]([N:39]=[N+:40]=[N-:41])(CCCC)CCCC)CCC>O1CCOCC1>[NH:39]1[C:1]([CH:3]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:4][C:5]([NH:7][C:8]2[C:9]([O:18][CH3:19])=[CH:10][C:11]([O:16][CH3:17])=[CH:12][C:13]=2[O:14][CH3:15])=[O:6])=[N:2][N:41]=[N:40]1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 86748282beta-cyano-N-(2,4,6-trimethoxyphenyl)benzene propanamide

Product 1

HCID 178493528HCID 178493528, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of the material from step (a) (5.1 g, 0.016 mol) in dioxane (150 mL) at room temperature was added tri-n-butyltin azide (9.36 g, 0.016 mol) under N2 with stirring. The resulting solution was heated to reflux for 24 hours. The solution was then cooled and concentrated in vacuo. The residue was redissolved in ether and HCl gas was then passed through the solution for 30 minutes. This was then concentrated in vacuo to give β-(1H-tetrazol-5-yl)-N-(2,4,6-trimethoxyphenyl)benzene propanamide as a white solid (2.1 g) which was used without further purification.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe solution was then cooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was redissolved in ether
  6. concentrationThis was then concentrated in vacuo

Sources & evidence

ORD record
ord-d78d4fc590ef4b47aca19d34941fe1f2
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

Loading…