Hydrochloric Acid → 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoic acid

HRID 607495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 607495
[C:1]([C:3]1[C:7](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5](=[O:19])[C:4]=1[C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH2:36][CH:37]([CH2:42][CH3:43])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[CH:22][CH:21]=1)#[N:2].O1CCCC1.Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl.O>[C:1]([C:3]1[C:7](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5](=[O:19])[C:4]=1[C:20]1[CH:21]=[CH:22][C:23]([N:26]([CH2:36][CH:37]([CH2:42][CH3:43])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:24][CH:25]=1)#[N:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 86634096methyl 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate

Produkt 1

HCID 866340926-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoic acidAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The prepared methyl 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate (7.5 g, 12.8 mmol) and tetrahydrofuran (50 ml) were loaded into a flask and stirred. Hydrochloric acid (20 ml, 3 N) was added thereto, and the mixture was allowed to react at 65° C. for 24 hours with stirring. The reaction product was transferred into a separate funnel, and was then added with water and dichloromethane, after which the organic layer was isolated therefrom, dehydrated using sodium sulfate, and then distilled under reduced pressure. Subsequently, the obtained material was separated through silica column chromatography, thus obtaining 6.4 g of a dark blue solid.

Aufarbeitung

  1. customto react at 65° C. for 24 hours
  2. stirringwith stirring
  3. customThe reaction product was transferred into a separate funnel
  4. customafter which the organic layer was isolated
  5. distillationdistilled under reduced pressure
  6. customSubsequently, the obtained material was separated through silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8938774dd67446dab117a875d1c8d759
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915428B2

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