Benzaldehyde → 2-methyl-N-benzylidene-propane-2-sulfinamide

HRID 1971318Notes

Reaction equation

HRID 1971318 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([S:13]([NH2:15])=[O:14])([CH3:12])[CH3:11]>C1COCC1.[Cl-].[Na+].O.CCO.CCO.CCO.CCO.[Ti]>[C:2]1([CH:1]=[N:15][S:13]([C:10]([CH3:12])([CH3:11])[CH3:9])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 240BenzaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 673910032-methyl-N-benzylidene-propane-2-sulfinamide

Reagents, catalysts & solvents 3

HCID 2724286Titanium(IV)ethoxideCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Benzaldehyde (6 mmol, 1 eq), 2-methyl-propane-2-sulfinic acid amide (1 eq) and tetraethyl orthotitanate (3 eq) are dissolved in anhydrous THF under nitrogen (J. Org. Chem. 2003, 68, 9948-9957). The mixture is stirred at room temperature over night. The mixture is poured in brine and stirred vigorously. The resulting suspension is filtered through Celite and the filter cake is extracted with ethyl acetate. The filtrate is transferred to a separatory funnel, where the aqueous layer is separated and extracted 3× with ethyl acetate. The organic layers are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. Tert.-butane-sulfinic acid 1-phenyl-methylidene amide is obtained as a clear yellowish oil (90% yield); ES-MS (MH+)=210.2; 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 8.56 (s, 1H), 7.96-7.93 (m, 2H), 7.63-7.53 (m, 3H), 1.19 (s, 9H).

Workup

  1. stirringstirred vigorously
  2. filtrationThe resulting suspension is filtered through Celite
  3. extractionthe filter cake is extracted with ethyl acetate
  4. customThe filtrate is transferred to a separatory funnel
  5. customwhere the aqueous layer is separated
  6. extractionextracted 3× with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c774d129bab4e9da0cb28ebbf9b6ce8
Source dataset
uspto-grants-2013_04
Patent number
US08431602B2

Reaction notes

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