Tributyltin azide → HCID 178493979, compound

HRID 1458562Notes

Reaction equation

HRID 1458562 reaction equation
[Cl:1][C:2]1[C:3]([N:17]([CH2:22][C:23]#[N:24])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2.C([Sn]([N:38]=[N+:39]=[N-:40])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([N:17]([CH2:22][C:23]2[NH:40][N:39]=[N:38][N:24]=2)[S:18]([CH3:21])(=[O:20])=[O:19])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 22097030HCID 22097030, compound

Product 1

HCID 178493979HCID 178493979, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(cyanomethyl)methanesulphonamide (100 mg, 0.256 mmol) and tributyltin azide (170 mg, 0.512 mmol) (Synthesis, 1976, 329) in toluene (10 ml) was heated at reflux for 18 hours. After cooling the mixture was concentrated under reduced pressure and the residue purified by flash chromatography (gradient elution from dichloromethane to 90:10:1 dichloromethane: methanol:ammonia) to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(5-tetrazolylmethyl) methanesulphonamide as an off-white solid (78 mg, 70%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling the mixture
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue purified by flash chromatography (gradient elution from dichloromethane to 90:10:1 dichloromethane: methanol:ammonia)

Sources & evidence

ORD record
ord-88e9a943bf4349b69984b75590d5ce76
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

Loading…