Pyridine → HCID 178468799, Verbindung

HRID 2119022

Reaktionsgleichung

Reaktionsgleichung von HRID 2119022
[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4].[C:16]([O:25][CH2:26][CH3:27])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:19].N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>O>[ClH:1].[CH2:26]([O:25][C:16]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][C:13]([C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][NH:2][C:3]([NH2:5])=[NH:4])[CH2:12][CH2:11]1)=[O:15])=[O:24])[CH3:27]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6877Ethyl 2-aminobenzoateHCID 10868DicyclohexylcarbodiimideHCID 178479474HCID 178479474, Verbindung

Produkt 1

HCID 178468799HCID 178468799, VerbindungAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (10.0 g, 0.042 mole) (which is prepared by the method as disclosed in Japanese Patent First Publication No. 19694/1977, C.A., 87, 53269x) and ethyl anthranilate (10.4 g, 0.063 mole) are added to pyridine (50 ml), and the mixture is stirred for a while, and thereto is added dicyclohexylcarbodiimide (13 g, 0.063 mole), and the mixture is stirred at room temperature for 72 hours. After the completion of the reaction, water (30 ml) is added to the reaction mixture, and the mixture is stirred for 30 minutes, and the undissolved materials are filtered off. The filtrate is concentrated to dryness. The resulting residue is washed with ethyl acetate (300 ml) and recrystallized from water to give the title compound (6.74 g) as white crystals. m.p. 92°-95° C.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 72 hours
  2. additionis added to the reaction mixture
  3. stirringthe mixture is stirred for 30 minutes
  4. filtrationthe undissolved materials are filtered off
  5. concentrationThe filtrate is concentrated to dryness
  6. washThe resulting residue is washed with ethyl acetate (300 ml)
  7. customrecrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-e94ce90f3b1545ac9c7615fd226e4cb5
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04681895

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