m-Formylbenzonitrile → HCID 66962498, compound

HRID 1360124Notes

Reaction equation

HRID 1360124 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[CH3:11][C:12]([S@@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>O1CCOCC1.[Cl-].[Na+].O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[N:17][S@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

5

Reactant 2

HCID 90670m-FormylbenzonitrileHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 66962498HCID 66962498, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

In a flame dried flask under N2, 3-cyanobenzaldehyde (7.050 g, 53.76 mmol) was dissolved in anhydrous dioxane (100 mL). Ti(IV) ethoxide (28.183 mL, 134.40 mmol) was added followed by (S)-(−)-2-methyl-2-propanesulfinamide (7.167 g, 59.14 mmol). The r×n was heated to 110° C. After 2.5 hr the reaction was cooled to RT and brine (150 mL) was added. A precipitate formed and the reaction was rapidly stirred for 1 hr. 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 aqueous layer was extracted with ethyl acetate (1×). The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo to afford (S)—N-[(3-cyanophenyl)methylidene]-2-methylpropane-2-sulfinamide as a light orange solid. 1H NMR (CD3OD) (8.61 (s, 1H), 8.26 (s, 1H), 8.22-8.20 (m, 1H), 7.94-7.92 (m, 1H), 7.72 (t, 1H, J=7.81 Hz), 1.28 (s, 9H).

Workup

  1. customIn a flame dried flask under N2
  2. temperatureAfter 2.5 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. extractionThe aqueous layer was extracted with ethyl acetate (1×)
  8. dry with materialThe combined organics were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d77e8c95613849c0a60a1fcfbea94bba
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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