Sodium Hydroxide → HCID 19095406, Verbindung

HRID 486517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486517
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH2:14][CH2:15][NH:16][C:17](=O)[CH3:18])[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>O.C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]3[CH2:14][CH2:15][N:16]=[C:17]([CH3:18])[C:11]3=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095262N-[2-[2-(4-Methoxyphenyl)-1H-pyrrol-1-yl]ethyl]acetamide

Produkt 1

HCID 19095406HCID 19095406, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

N-[2-[2-(p-Methoxyphenyl)-pyrrol-1-yl]ethyl]-acetamide (2.1 g) was treated with 10 ml of phosphorus oxychloride under argon and boiled for 1/2 hour while stirring. The reaction mixture was hydrolyzed at 0° C. with 100 ml of 2N sodium hydroxide solution and 50 ml of 28% sodium hydroxide solution, diluted with 600 ml of water and extracted three times with 100 ml of methylene chloride each time. The organic extracts were combined, dried with MgSO4 and freed from solvent. 1.0 g of a total of 2.0 g of crude product was dissolved in a 40-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.6 g (42%) of 3,4-dihydro-6-(p-methoxyphenyl)-1-methyl-pyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 167°-169° C. (dec.).

Aufarbeitung

  1. extractionextracted three times with 100 ml of methylene chloride each time
  2. dry with materialdried with MgSO4
  3. dissolution1.0 g of a total of 2.0 g of crude product was dissolved in a 40-fold amount of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8d1acd49ce3b4d6886cf8fd5984397f2
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292732

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