Hexane → 2-Benzoyl-benzoic acid N',N'-dimethyl-hydrazide

HRID 44434

Reaktionsgleichung

Reaktionsgleichung von HRID 44434
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][N:10]([CH3:22])[N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21].CCCCCC>C1COCC1>[CH3:22][N:10]([CH3:9])[NH:11][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:12](=[O:21])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 8058HexaneHCID 2489762-(Dimethylamino)isoindoline-1,3-dioneHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 90925702-Benzoyl-benzoic acid N',N'-dimethyl-hydrazideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution of phenylmagnesium bromide in THF (11.6 mmol) was slowly added to a solution of phthalimide 16 (10.5 mmol) in THF (110 ml) at −78 ° C. and stirred under argon for 15 minutes. The mixture was then progressively warmed to −30 ° C. for 1 hour. The reaction was quenched with a saturated aqueous solution of NH4Cl (15 ml) and the aqueous layer extracted with Et2O. The combined organic layers were washed with brine (20 ml), dried over MgSO4 and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography with (1:2) EtOAc:hexane, to give 80% yield of the desired product.

Aufarbeitung

  1. customThe reaction was quenched with a saturated aqueous solution of NH4Cl (15 ml)
  2. extractionthe aqueous layer extracted with Et2O
  3. washThe combined organic layers were washed with brine (20 ml)
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography with (1:2) EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3976c3e264b3492f8f54258f8d544731
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541428B2

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