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

HRID 559725Notes

Reaction equation

HRID 559725 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-e8b1700516fe4169a09ec17fa40fda6a
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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