Dicyclohexylcarbodiimide → HCID 20563557, Verbindung

HRID 1154946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1154946
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH2:13][CH2:14][C:15](=[O:21])[NH:16]2)([OH:3])=O.[CH2:22]([NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH:30]1([N:29]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH2:13][CH2:14][C:15](=[O:21])[NH:16]3)=[O:3])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 204463Benzenemethanamine, N-cyclohexyl-HCID 12819300HCID 12819300, Verbindung

Produkt 1

HCID 20563557HCID 20563557, VerbindungAusbeute 23,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 2.9 g of 5-(6-carboxyhexyloxy)-3,4-dihydrocarbostyril and 1.9 g of N-benzylcyclohexylamine in 100 ml of DMF is added gradually dropwise a solution of 2.1 g of N,N'-dicyclohexylcarbodiimide in 10 ml of DMF at room temperature and under agitation. After this agitation, the mixture is further agitated at room temperature for 5 hours. After the reaction, the insolubles are filtered off and the mother liquor is concentrated. The residue is dissolved in chloroform and subjected to silica gel thin-layer chromatography (solvent: chloroform-methanol (8:1) to scrape out the portion with Rf value of 0.8. The silica gel is extracted with chloroform, and after distilling off chloroform, the residue is recrystallized from benzene-ligroin to obtain 1.1 g of 5-[6-(N-cyclohexyl-N-benzylaminocarbonyl)hexyloxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 49°-52° C.

Aufarbeitung

  1. customAfter the reaction
  2. filtrationthe insolubles are filtered off
  3. concentrationthe mother liquor is concentrated
  4. dissolutionThe residue is dissolved in chloroform
  5. extractionThe silica gel is extracted with chloroform
  6. distillationafter distilling off chloroform
  7. customthe residue is recrystallized from benzene-ligroin

Quellen und Nachweise

ORD-Eintrag
ord-add44c1406b14d88bdea036fe2dcc5e0
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04298739

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