Sodium Chloride → HCID 118023402, compound

HRID 1498873Notes

Reaction equation

HRID 1498873 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[F:8][C:9]([F:20])([F:19])[C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O.[Na+].[Cl-].CCOC(C)=O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][C:2]([S@:5](/[N:7]=[C:10](/[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)\[C:9]([F:8])([F:20])[F:19])=[O:6])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 118023402HCID 118023402, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(R)-2-Methylpropane-2-sulfinamide (0.64 g, 5.28 mmol), 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone (0.53 g, 2.76 mmol) and titanium(IV) isopropoxide (1.5 mL, 5.12 mmol) were stirred in THF (13 mL) at 70° C. for 18 hours. Room temperature was attained, saturated NaCl and EtOAc were added, and the resulting biphasic suspension was stirred for 5 minutes. The suspension was filtered through Celite to remove the titanium residues, and the organic phase was separated. The aqueous phase was extracted a second time with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo while loading onto silica. Purification of the residue by MPLC (0-20% EtOAc-hexanes) gave (R,Z)-2-methyl-N-(2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene)propane-2-sulfinamide (0.23 g, 0.779 mmol, 28.2% yield) as a yellow oil.

Workup

  1. customRoom temperature
  2. filtrationThe suspension was filtered through Celite
  3. customto remove the titanium residues
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was extracted a second time with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue by MPLC (0-20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-f8c9c9b3a06842a897a9ba7a0b934dcb
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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