Phenol → HCID 178479472, Verbindung

HRID 1702606

Reaktionsgleichung

Reaktionsgleichung von HRID 1702606
[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4].[C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4]

Komponenten

5

Edukt 3

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 178479474HCID 178479474, Verbindung

Produkt 1

HCID 178479472HCID 178479472, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A suspension of trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (11.8 g), phenol (5.6 g), and dicyclohexylcarbodiimide (12.4 g) in pyridine (75 ml) was stirred overnight at room temperature. After evaporation of solvent, the residue was treated with 0.1 N hydrochloric acid (200 ml), the insoluble materials removed by filtration and the filtrate was washed with ethylacetate. The aqueous layer was concentrated to 100 ml, the resulting crystals were filtered and washed with isopropylalcohol/isopropylether to give phenyl trans-4-guanidinomethylcyclohexanecarboxylate hydrochloride (12.5 g, 80.2%), m.p. 150°-153° C. This compound was recrystallized from methanol to give white crystal, phenyl trans-4-guanidinomethylcyclohexanecarboxylate hydrochloride, m.p. 159.5°-161.5° C.

Aufarbeitung

  1. customAfter evaporation of solvent
  2. additionthe residue was treated with 0.1 N hydrochloric acid (200 ml)
  3. customthe insoluble materials removed by filtration
  4. washthe filtrate was washed with ethylacetate
  5. concentrationThe aqueous layer was concentrated to 100 ml
  6. filtrationthe resulting crystals were filtered
  7. washwashed with isopropylalcohol/isopropylether

Quellen und Nachweise

ORD-Eintrag
ord-281cb1d74fd14f1ab2f24d483ac632e2
Quelldatensatz
uspto-grants-1982_09
Patentnummer
US04348410

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