Hydrochloric Acid → Levosimendan

HRID 1467372

Reaktionsgleichung

Reaktionsgleichung von HRID 1467372
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Cl.[N:17]([O-])=O.[Na+].[C:21](#[N:25])[CH2:22][C:23]#[N:24].C([O-])(=O)C.[Na+]>>[CH3:15][C@H:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][N:17]=[C:22]([C:21]#[N:25])[C:23]#[N:24])=[CH:3][CH:4]=2)=[N:13][NH:12][C:11](=[O:14])[CH2:10]1

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 161928Ici 109,081HCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 3033825LevosimendanAusbeute 82,3 %

Versuchsvorschrift

To a solution of (−)-6-(4-aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone (20 g) and dilute hydrochloric acid (52 ml of concentrated hydrochloric acid in 789 ml of water), 8 g of dilute sodium nitrite (8 g of sodium nitrite in 52 ml of water) was added and stirred. After 10 minutes, malononitrile solution (6.3 g malononitrile in 52 ml of water) was added. The solution was stirred for 1 hour at room temperature. The pH of the suspension was adjusted to 6.0 with sodium acetate solution. The suspension was filtered, washed with water followed by ethanol and then dried to obtain solid levosimendan (yield—22 g, purity—99.9%).

Aufarbeitung

  1. stirringThe solution was stirred for 1 hour at room temperature
  2. filtrationThe suspension was filtered
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4647ec44381243a985154d5e0c3f01f6
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000158B2

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