Diethyl (ethoxymethylene)malonate → HCID 178524753, Verbindung

HRID 1525309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525309
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[NH:10])[NH2:9])[N:3]=1.C([O:13][CH:14]=[C:15]([C:21](OCC)=O)[C:16]([O:18]CC)=[O:17])C.C[O-].[Na+].[OH-].[K+]>CO>[OH:13][C:14]1[C:15]([C:16]([OH:18])=[O:17])=[CH:21][N:9]=[C:8]([C:4]2[N:3]=[N:2][CH:7]=[CH:6][CH:5]=2)[N:10]=1

Komponenten

6

Edukt 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 18756080Pyridazine-3-carboximidamide hydrochloride

Produkt 1

HCID 178524753HCID 178524753, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of crude Pyridazine-3-carboximidamide hydrochloride, 30-id, (4.2 g, 34.4 mmol), diethyl ethoxymethylenemalonate (6.5 mL, 34.4 mmol) and sodium methoxide (1.85 g, 41.3 mmol) in MeOH (100 mL) was refluxed overnight. The reaction mixture was added with KOH (3.8 g, 68.8 mmol) and refluxed for 4 h. The reaction was concentrated. The residue was dissolved with water (30 mL) and extracted with EtOAc. The aqueous layer was adjusted to pH=2 by addition of concentrated aq. HCl. The solids was filtered and rinsed with water and hexane to afford the title compound, 30-ie, (3 g, 40%). 1H NMR (300 MHz, CD3OD) δ14.7 (s, 1H), 9.50 (dd, J=1.6, 5.0 Hz), 8.57 (s, 1H), 8.51 (dd, J=1.6, 8.4 Hz, 1H), 8.01 (dd, J=5.0, 8.4 Hz, 1H), 3.44 (s, 1H). LC-MS: (M+H)+ 219.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. temperaturerefluxed for 4 h
  3. concentrationThe reaction was concentrated
  4. dissolutionThe residue was dissolved with water (30 mL)
  5. extractionextracted with EtOAc
  6. additionThe aqueous layer was adjusted to pH=2 by addition of concentrated aq. HCl
  7. filtrationThe solids was filtered
  8. washrinsed with water and hexane

Quellen und Nachweise

ORD-Eintrag
ord-caf8299568e04755ace760187a49f00a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079930B2

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