Pyridine → HCID 178497648, Verbindung

HRID 2119023

Reaktionsgleichung

Reaktionsgleichung von HRID 2119023
[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][CH3:26])(=[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].[CH3:26][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]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8635Methyl AnthranilateHCID 10868DicyclohexylcarbodiimideHCID 178479474HCID 178479474, Verbindung

Produkt 1

HCID 178497648HCID 178497648, VerbindungAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (3 g, 0.013 mole) (which is prepared by the method as disclosed in Japanese Patent First Publication No. 19694/1977, C.A., 87, 53269x) and methyl anthranilate (2.3 g, 0.015 mole) are added to pyridine (20 ml), and the mixture is stirred for a while, and thereto is added dicyclohexylcarbodiimide (3.1 g, 0.015 mole), and the mixture is stirred at room temperature for 72 hours. After the completion of the reaction, water (10 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 (100 ml) and recrystallized from water to give the title compound (2.23 g) as white crystals. m.p. 118.5°-120.5° 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 (100 ml)
  7. customrecrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-744d9ce5058b406d8f45319bd435d81a
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04681895

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