Water → (R,E)-N-(1-(5-bromo-2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide

HRID 1992269Notes

Reaction equation

HRID 1992269 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].O>C1COCC1>[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([F:11])=[C:6]([C:8](=[N:19][S@@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 207853591-(5-Bromo-2,4-difluorophenyl)ethan-1-one

Product 1

HCID 86635612(R,E)-N-(1-(5-bromo-2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamideYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(5-bromo-2,4-difluoro-phenyl)-ethanone (19 g, 64.7 mmoles, 1 equiv.) and (R)-2-methyl-propane-2-sulfinic acid amide (10.2 g, 84.1 mmoles, 0.76 equiv) in THF (0.3 M, 215 mL) is added Ti(OEt)4 (29.5 g, 129 mmoles, 2.0 equiv) in a single portion at ambient temperature. The reaction is heated to 70° C. and allowed to stir 18 h. The reaction is cooled to ambient temperature, and poured into water. The resulting suspension is filtered through a pad of diatomaceous earth and washed with ethyl acetate. The filtrate is collected and extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel chromatography, eluting with a linear gradient of hexane to hexane:ethyl acetate (3:1) over 20 minutes to give the title compound (81% yield): MS (m/z): 338, 340 (M+1).

Workup

  1. temperatureThe reaction is cooled to ambient temperature
  2. filtrationThe resulting suspension is filtered through a pad of diatomaceous earth
  3. washwashed with ethyl acetate
  4. customThe filtrate is collected
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a residue
  10. customThe residue is purified by silica gel chromatography
  11. washeluting with a linear gradient of hexane to hexane:ethyl acetate (3:1) over 20 minutes

Sources & evidence

ORD record
ord-0ba8c189cec94ce1af74de2431b16409
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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