Phenylglyoxylic Acid → N'-t-butyl-N-benzoylcarbonyl-N'-benzoylhydrazine

HRID 21666

Reaktionsgleichung

Reaktionsgleichung von HRID 21666
C([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(C)(C)C.[C:15]([C:23]([OH:25])=O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:8]([N:6]([C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:5][C:23]([C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:25])([CH3:13])([CH3:9])[CH3:7]

Komponenten

7

Edukt 4

HCID 11915Phenylglyoxylic AcidHCID 31297Methanesulfonyl chlorideHCID 299436N'-tert-butylbenzohydrazideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 19367969N'-t-butyl-N-benzoylcarbonyl-N'-benzoylhydrazineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

N'-t-butyl-N-benzoylhydrazine (1 g), benzoyl formic acid (1 g) and methanesulfonyl chloride (0.7 g) were stirred in toluene (35 ml) and saturated sodium bicarbonate (15 ml) at approximately 5° C. Triethylamine was added slowly, dropwise to the reaction mixture, and slowly warmed to room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (20 ml) and the organic layer was washed several times with water. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white gum. The crude product was chromatographed on silica gel (G:230-400 mesh) using a methylene chloride ether solvent system as eluant to afford a 65% yield of a white solid.

Aufarbeitung

  1. customat approximately 5° C
  2. washthe organic layer was washed several times with water
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customto afford a white gum
  6. customThe crude product was chromatographed on silica gel (G:230-400 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-5c1f70365848435ead7e43c74e189906
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424333

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