Hydrochloric Acid → HCID 60102483, Verbindung

HRID 510409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510409
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[Cl:6][C:7]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.[BH4-].[Na+].Cl>C(O)C.O>[Cl:6][C:7]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][CH:2]([C:1]#[N:5])[C:3]#[N:4]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 357452,3-DichlorobenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 60102483HCID 60102483, VerbindungAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of malononitrile (2.64 g, 40 mmol) in 95% Ethanol (50 mL) was added 2,3-dichlorobenzaldehyde (7.00 g, 40.0 mmol). The reaction was stirred at rt for 18 h. EtOH (20 mL) was added and the mixture was stirred at rt for 20 min and cooled to 0° C. in an ice bath. Sodium borohydride (0.424 g, 11.20 mmol) was introduced to the vigorously stirred mixture and the reduction was complete in about 10 min. To the reaction mixture was added water (40 mL). 1N HCl was added in to quench the excess hydride. More water was added in until precipitation was complete. Filtration gave [(2,3-dichlorophenyl)methyl]propanedinitrile (7.86 g, 87%). To a solution of [(2,3-dichlorophenyl)methyl]propanedinitrile (7.86 g, 34.9 mmol) in Ethanol (80 mL) was added hydrazine hydrate (2.57 mL, 52.4 mmol). The mixture is heated at reflux temperature for 8 h. The reaction mixture was concentrated. The crude material was purified on a silica column (MeOH/DCM: 0˜10%) to give the product (4.2 g, 47%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 3.77 (s, 2H) 7.09 (m, 1H) 7.19 (t, J=7.96 Hz, 1H) 7.38 (m, 1H); LC/MS: MS (ES+) m/e 257.0 [M+H]+.

Aufarbeitung

  1. stirringthe mixture was stirred at rt for 20 min
  2. temperaturecooled to 0° C. in an ice bath
  3. waitthe reduction was complete in about 10 min
  4. customto quench the excess hydride
  5. additionMore water was added in until precipitation
  6. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-838d63a27c5f42bca00ad6da576d4342
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096605B2

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