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

HRID 1616231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616231
[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]

Komponenten

6

Edukt 2

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

Produkt 1

HCID 89735588HCID 89735588, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11026Titanium isopropoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ab72164f2db444778f3b9a6e6b4dcbe1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765784B2

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