Water → N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide

HRID 2067956Notes

Reaction equation

HRID 2067956 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=O)[CH:12]=[N:13][CH:14]=1.O>ClCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH:12]=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 66745079N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamideYield 101.4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methyl-propane-2-sulfinamide (11 g, 91 mmol) and 5-bromo-3-pyridine-carboxaldehyde (14 g, 75 mmol) in dichloromethane (500 mL) is added titanium isopropoxide (43 g, 150 mmol). The reaction is then heated at reflux (bath temperature=60° C.) for 4 hours. The resultant mixture is cooled to room temperature and poured into a stirred mixture of diatomaceous earth (50 g) and water (150 mL). The slurry is stirred for 10 min and then filtered. The organic layer from the filtrate is washed with brine and dried over sodium sulfate. Filtration and concentration in vacuo affords 2-methyl-propane-2-sulfinic acid 1-(5-bromo-pyridin-3-yl)-methylideneamide as a yellow solid (22 g, 99%).

Workup

  1. temperatureThe reaction is then heated
  2. filtrationfiltered
  3. washThe organic layer from the filtrate is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-041ebdf1c90a4785a9300089f5e88c8d
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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