Ethylenediamine → HCID 72714946, Verbindung

HRID 77359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77359
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:5][N:4]2[C:18]([C:21]#[N:22])=[CH:19][CH:20]=[C:3]12.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.[CH2:37](N)[CH2:38][NH2:39]>>[NH:22]1[CH2:37][CH2:38][N:39]=[C:21]1[C:18]1[N:4]2[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:10][CH:9]=3)[NH:7][C:2](=[O:1])[C:3]2=[CH:20][CH:19]=1

Komponenten

4

Edukt 3

HCID 3301EthylenediamineHCID 14817Phosphorus sulfide (P2S5)HCID 727149431-Oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile

Produkt 1

HCID 72714946HCID 72714946, VerbindungAusbeute 81,8 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 1-oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile (Example 2) (0.03 g, 98.9 μmol), phosphorus pentasulfide (8 mg, 36.0 μmol) and ethane-1,2-diamine (0.5 mL, 7.48 mmol) in a sealed vial was heated at 120° C. for 2 h. At this time, the green/yellow reaction mixture was allowed to cool to room temperature and was then poured onto ice water. The resulting solid was collected by filtration, washed with water and dried in vacuo to afford 6-(4,5-dihydro-1H-imidazol-2-yl)-3-(4-trifluoromethyl-phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one (28 mg, 81%) as light yellow solid. 1H NMR (methanol-d4) δ ppm 7.86-7.91 (m, 3H), 7.77-7.84 (m, 3H), 7.44 (d, J=0.8 Hz, 1H), 3.81 (s, 4H). LC-MS calcd. for C17H14F3N4O [(M+H)+] 347, obsd. 347.0.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. additionwas then poured onto ice water
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7f6780835ef6485ca92a327edb2542a4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841299B2

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