Benzophenone → HCID 86602991, compound

HRID 2099582Notes

Reaction equation

HRID 2099582 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]([S@@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17]>O1CCOCC1.[Cl-].[Na+].O>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:21][S@:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3102BenzophenoneHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 86602991HCID 86602991, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
105 °C

Procedure

In a flame dried flask under N2, benzophenone (0.514 g, 2.82 mmol) was dissolved in anhydrous dioxane (5 mL). Ti(IV) ethoxide (1.479 mL, 7.05 mmol) was added followed by (S)-(−)-2-methyl-2-propanesulfinamide (0.376 g, 3.10 mmol). The rxn was heated to 105° C. After 4.5 hr the reaction was cooled to RT and brine (15 mL) was added. A precipitate formed and the reaction was rapidly stirred for 10 min. The suspension was filtered through celite and the filter cake was washed with brine and ethyl acetate. The layers of the filtrate were separated. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford a yellow oil. The oil was purified by flash column chromatography (90:10 hexanes/ethyl acetate). The fractions were combined and concentrated in vacuo to afford (S)-N-(diphenylmethylene)-2-methylpropane-2-sulfinamide as a light yellow oil. 1H NMR (CDCl3) δ 7.51-7.43 (broad m, 10H), 1.30 (s, 9H). [M+H]+=286.1.

Workup

  1. customIn a flame dried flask under N2
  2. temperatureAfter 4.5 hr the reaction was cooled to RT
  3. customA precipitate formed
  4. filtrationThe suspension was filtered through celite
  5. washthe filter cake was washed with brine and ethyl acetate
  6. customThe layers of the filtrate were separated
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford a yellow oil
  11. customThe oil was purified by flash column chromatography (90:10 hexanes/ethyl acetate)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93797cb7d343407fa1905d87c7c39206
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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