Dibutyltin oxide → HCID 178523120, compound

HRID 1869807Notes

Reaction equation

HRID 1869807 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:3]=1[C:4]([NH:6][CH:7]([C:27]#[N:28])[CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])[CH:13]=[CH:12]2)=[O:5].C[Si]([N:38]=[N+:39]=[N-:40])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:3]=1[C:4]([NH:6][CH:7]([C:27]1[NH:40][N:39]=[N:38][N:28]=1)[CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])[CH:13]=[CH:12]2)=[O:5]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 685928212,6-dichloro-N-{1-cyano-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]ethyl}benzamide

Product 1

HCID 178523120HCID 178523120, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2,6-dichloro-N-{1-cyano-2-[2-(2,6-dichlorophenyl)-6-quinolinyl]ethyl}benzamide 58 (0.358 g) in toluene (5 ml) are added trimethylsilyl azide (184 μl) and dibutyltin oxide (17 mg). The solution is heated at reflux overnight, then evaporated under vacuum. The resulting residue is purified twice over silica gel using one time CH2Cl2/CH3OH 85/15 as eluent and the second time CH2Cl2/(CH3OH-10% NH4OH) 85/15 to give 2,6-dichloro-N-[2-[2-(2,6-dichlorophenyl)-6-quinolinyl]-1-(1H-tetraazol-5-yl)ethyl]benzamide 126.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux overnight
  3. customevaporated under vacuum
  4. customThe resulting residue is purified twice over silica gel using one time CH2Cl2/CH3OH 85/15 as eluent

Sources & evidence

ORD record
ord-e6989520636a409ca3828782f49a737b
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

Loading…