Diphenylphosphinic chloride → HCID 9908920, Verbindung

HRID 1458293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458293
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH:37]1[CH2:41][N:40]([CH2:42][CH3:43])[N:39]([CH2:44][CH3:45])[CH2:38]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:44]([N:39]1[CH2:38][CH:37]([NH:36][C:16](=[O:18])[C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])=[CH:20][CH:19]=2)[CH2:41][N:40]1[CH2:42][CH3:43])[CH3:45]

Komponenten

6

Edukt 3

HCID 73910Diphenylphosphinic chlorideHCID 5591991,2-Diethyl-4-pyrazolidinamineHCID 123615004-Geranyloxybenzoic acid

Produkt 1

HCID 9908920HCID 9908920, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 4- geranyloxybenzoic acid (1.10 g) in chloroform (20 ml), triethylamine (1.11 ml) and a solution of diphenylphosphinic chloride (0.95 g) in chloroform (5 ml) were successively added. After the reaction solution was stirred for 30 minutes, 4-amino-1,2-diethylpyrazolidine (0.57 g) was added and then the mixture was stirred at room temperature for one night. The reaction solution was washed with aqueous solution of sodium hydrogencarbonate, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) and then recrystallized from n-hexane, thereby yielding 1.39 g (87%) of the aimed compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for one night
  2. washThe reaction solution was washed with aqueous solution of sodium hydrogencarbonate
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated under a vacuum
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  6. customrecrystallized from n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0f04536133ba4aacbd4d438ea0cc9951
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849930

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