Guanidine Hydrochloride → HCID 18945407, Verbindung

HRID 399865

Reaktionsgleichung

Reaktionsgleichung von HRID 399865
[ClH:1].[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[C:9]1([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[C:18](OC)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C>CO.O>[ClH:1].[C:9]1([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=2)[C:18]([N:4]=[C:3]([NH2:5])[NH2:2])=[O:19])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 8857Ethyl AcetateHCID 9855857Methyl 3-phenylbenzoateHCID 10942334Sodium Methoxide

Produkt 1

HCID 18945407HCID 18945407, VerbindungAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of guanidine hydrochloride (2.7 g) in methanol (12 ml) was added sodium methoxide (5.13 g, 28% in methanol) and the mixture was stirred for 15 minutes under nitrogen. To this mixture was added a solution of methyl 3-phenylbenzoate (1.20 g) in methanol (2 ml) and the mixture was stirred for 6 hours. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (50 ml). The organic layer was successively washed with 5N-sodium hydroxide aqueous solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on alumina (100 ml) and eluted with chloroform-methanol (10:1). The fractions containing the desired product were collected and evaporated in vacuo. The residue was crystallized from 4N-hydrogen chloride-ethyl acetate. The crystalline was recrystallized from ethanol to afford 2-[3-phenylbenzoyl]guanidine hydrochloride (274.0 mg).

Aufarbeitung

  1. stirringthe mixture was stirred for 6 hours
  2. washThe organic layer was successively washed with 5N-sodium hydroxide aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on alumina (100 ml)
  6. washeluted with chloroform-methanol (10:1)
  7. additionThe fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo
  10. customThe residue was crystallized from 4N-hydrogen chloride-ethyl acetate
  11. customThe crystalline was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0e2f8d909e844621b2cc05d5ca6ce18e
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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