Hydrochloric Acid → 2-(4-Chlorophenyl)thieno[2,3-d]pyridazin-7(6H)-one

HRID 2239329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239329
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](O)=[O:14])=[C:10]([CH:16]=O)[CH:9]=2)=[CH:4][CH:3]=1.O.[NH2:19][NH2:20].Cl.C([O-])(O)=O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:14])[NH:19][N:20]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 593044065-(4-Chlorophenyl)-3-formylthiophene-2-carboxylic acid

Produkt 1

HCID 115798042-(4-Chlorophenyl)thieno[2,3-d]pyridazin-7(6H)-oneAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

To a stirred solution of 5-(4-chlorophenyl)-3-formylthiophene-2-carboxylic acid (3 g, 0.011 mol) in ethanol (30 ml) was added hydrazine hydrate (0.65 ml, 0.013 mol) in small drops. To this was added conc. HCl (1.8 ml, 0.058 mol) in a dropwise manner and heated to 82° C. for 2 days. The reaction mixture was allowed to cool down and 10% NaHCO3 (5 ml) was added slowly until pH=8. The solid was filtered, washed with water (200 ml) and dried to afford 2.1 g (71%) of the title compound. Rf=0.5 (CHCl3:MeOH, 8:2). 1H NMR (400 MHz, DMSO-d6) δ 12.98 (bs, 1H), 8.39 (s, 1H), 7.98 (s, 1H), 7.88 (d, 2H, J=8.6 Hz), 7.59 (d, 2H, J=8.6 Hz).

Aufarbeitung

  1. temperatureto cool down
  2. filtrationThe solid was filtered
  3. washwashed with water (200 ml)
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-54844651b2ae45009d9a509b1740fa2e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723331B2

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