Dibutyltin oxide → HCID 118308772, compound

HRID 923498Notes

Reaction equation

HRID 923498 reaction equation
[C:1]([C:3]1([CH3:17])[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])#[N:2].C[Si]([N:22]=[N+:23]=[N-:24])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:8][C:5]1([CH3:9])[N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:3]([CH3:17])([C:1]2[N:22]=[N:23][NH:24][N:2]=2)[CH2:7][O:6]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 118308689HCID 118308689, compound

Product 1

HCID 118308772HCID 118308772, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 317 mg of tert-butyl 4-cyano-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate, 307 mg of trimethylsilyl azide, 67 mg of dibutyltin oxide, and 10 ml of toluene was stirred for 8 hours under heating to reflux. The reaction mixture was left to be cooled to room temperature and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 168 mg of tert-butyl 2,2,4-trimethyl-4-(2H-tetrazol-5-yl)-1,3-oxazolidine-3-carboxylate.

Workup

  1. temperatureunder heating to reflux
  2. waitThe reaction mixture was left
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-73fb459e234a4b41835a6471755fbcd3
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…