tert-Butylsulfinamide, (S)-(-)- → HCID 89735588, compound

HRID 1616231Notes

Reaction equation

HRID 1616231 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([Br:12])[CH:5]=1)(=O)[CH3:2].[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.CCOC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:12][C:6]1[CH:5]=[C:4](/[C:1](=[N:19]/[S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])/[CH3:2])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 133472764-Acetyl-2-bromobenzonitrile

Product 1

HCID 89735588HCID 89735588, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-acetyl-2-bromobenzonitrile (4.0 g, 18 mmol) and (S)-2-methylpropane-2-sulfinamide (2.4 g, 20 mmol) in THF (35 mL) was added titanium(IV) isopropoxide (8.1 mL, 36 mmol) and the reaction mixture was heated to 40 C under an atmosphere of nitrogen. After 2 hours, the reaction was cooled to room temperature, diluted in EtOAc, washed with saturated sodium bicarbonate, rochelle's salt, brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography gave desired product. MS (M+H)+: observed=327.0/329.0, calculated=327.2/327.2.

Workup

  1. temperaturethe reaction mixture was heated to 40 C under an atmosphere of nitrogen
  2. washwashed with saturated sodium bicarbonate, rochelle's salt, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-ab72164f2db444778f3b9a6e6b4dcbe1
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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