Methanol → HCID 67981364, compound

HRID 2406932Notes

Reaction equation

HRID 2406932 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([S:14]([NH2:16])=[O:15])([CH3:13])[CH3:12].CO.C(=O)(O)[O-].[Na+]>ClCCl.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:16][S:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 966574-IodobenzaldehydeHCID 516892Sodium BicarbonateHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 67981364HCID 67981364, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Iodobenzaldehyde (1.26 g, 5.43 mmol) was dissolved in dichloromethane (41.8 mL). 2-methylpropane-2-sulfinamide (0.679 g, 5.43 mmol) was added, followed by titanium(IV) ethoxide (2.25 mL, 10.9 mmol). The reaction was heated to reflux for 1 hour. The reaction was then allowed to cool to room temperature and stir for 18 hours. Methanol (8.0 mL) and saturated sodium bicarbonate (1.5 mL) were added to the reaction mixture. The resulting slurry was filtered through sodium sulfate, and rinsed with ethyl acetate. The filtrate was concentrated to yield the title compound N-(4-iodobenzylidene)-2-methylpropane-2-sulfinamide (1.69 g, 93%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 8.51 (s, 1H), 7.80-7.84 (m, 2H), 7.53-7.57 (m, 2H), 1.25 (s, 9H). MS (M+1): 336.0.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe resulting slurry was filtered through sodium sulfate
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c7a6cdd812d34d9aa8a1ea2500ab9c55
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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