Carbon Disulfide → HCID 178504226, Verbindung

HRID 1890951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890951
[CH3:1][Si:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=2)[CH:9]=[N:8]1.C([O-])([O-])=O.[K+].[K+].[C:28](=S)=[S:29]>C(O)C.O>[CH3:1][Si:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:28]([SH:29])=[N:19][N:18]=3)[N:17]=2)[CH:9]=[N:8]1

Komponenten

6

Edukt 3

HCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 68975416{6-[1-(2-Trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-pyridazin-3-yl}-hydrazine

Produkt 1

HCID 178504226HCID 178504226, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of {6-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-pyridazin-3-yl}-hydrazine (490 mg, 1.6 mmol) in ethanol (6.5 mL) and water (1.8 mL) was added K2CO3 (359 mg, 2.6 mmol), followed by CS2 (0.212 mL, 3.5 mmol). The mixture was stirred and heated at 80° C. for 3 h under nitrogen atmosphere. The mixture was cooled to room temperature and concentrated to 50% volume in vacuo and acidified to pH 1 with 1 N aqueous HCl. The resulting precipitate was collected, washed with water, and dried in vacuo to provide title compound as a dark red solid (quantitative yield): 1H NMR (DMSO-d6) δ 0.01 (9H, s), 0.90 (2H, t), 3.63 (2H, t), 5.56 (2H, s), 7.82 (1H, d), 8.24 (1H, d), 8.27 (1H, s), 8.80 (1H, s), 15.23 (1H, bs); MS (m/z) 349 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated to 50% volume in vacuo
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1bef38ff57354014950cc9e49ea2df5f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507489B2

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