tert-Butylsulfinamide, (R)-(+)- → HCID 178458099, compound

HRID 1698224Notes

Reaction equation

HRID 1698224 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH3:17])=[N:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:20][C:21]([S@:24]([NH2:26])=[O:25])([CH3:23])[CH3:22]>ClC(Cl)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12](/[C:15](=[N:26]/[S:24]([C:21]([CH3:23])([CH3:22])[CH3:20])=[O:25])/[CH2:16][CH3:17])=[N:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 592780911-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propan-1-one

Product 1

HCID 178458099HCID 178458099, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propan-1-one (2.10 g, 7.55 mmol) in dichloroethane was added (R)-(+)-2-methyl-2-propanesulfinamide (1.45 g, 12.00 mmol) and titanium (IV) isopropoxide (4.26 g, 15.00 mmol) and the mixture was warmed at reflux overnight. After cooling, the solvent was concentrated in vacuo. The residue was diluted with EtOAc and saturated aqueous NaCl was added dropwise. After 20 minutes, the solution was passed through diatomaceous earth. The combined organics were washed with brine and dried over sodium sulfate. The solvent was concentrated in vacuo to afford 2-methyl-propane-2-sulfinic acid [1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-prop-(E)-ylidene]-amide.

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. concentrationthe solvent was concentrated in vacuo
  5. additionThe residue was diluted with EtOAc and saturated aqueous NaCl
  6. additionwas added dropwise
  7. washThe combined organics were washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-73e642b4d95c4e46be46d45e0254a3c7
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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