Tert-Butanesulfinamide → HCID 178455565, compound

HRID 522163Notes

Reaction equation

HRID 522163 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=O)[N:3]=[N:2]1.[CH3:8][C:9]([S:12]([NH2:14])=[O:13])([CH3:11])[CH3:10]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[NH:1]1[CH:5]=[C:4]([CH:6]=[N:14][S:12]([C:9]([CH3:11])([CH3:10])[CH3:8])=[O:13])[N:3]=[N:2]1

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 178519887HCID 178519887, compound

Product 1

HCID 178455565HCID 178455565, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1H-1,2,3-triazole-4-carbaldehyde (1 g, 10.3 mmol) and 2-methylpropane-2-sulfinamide (1.25 g, 10.3 mmol) were dissolved in tetrahydrofuran (20 mL). Titanium tetraisopropoxide (3.1 mL, 10.5 mmol) was added and the reaction heated at reflux for 8 hours. After cooling to room temperature, the reaction was quenched by adding saturated aqueous sodium chloride solution (5 mL) followed by dilution with tetrahydrofuran (80 mL) and stirred for 30 minutes. The mixture was filtered through a pad of Arbocel and the filtrate concentrated in vacuo, azeotroping with THF to afford the title compound (2.02 g, 98%).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 8 hours
  3. customthe reaction was quenched
  4. additionby adding saturated aqueous sodium chloride solution (5 mL)
  5. filtrationThe mixture was filtered through a pad of Arbocel
  6. concentrationthe filtrate concentrated in vacuo
  7. customazeotroping with THF

Sources & evidence

ORD record
ord-49689f2ca671408b997a6dc9f06b17a4
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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