Hydrazine hydrate (1:1) → HCID 89733627, Verbindung

HRID 573930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573930
[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N:11]=[C:12]=[S:13])[CH3:2].O.[NH2:15][NH2:16]>C(O)C>[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][C:12]([NH:15][NH2:16])=[S:13])[CH3:2]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 83799798HCID 83799798, Verbindung

Produkt 1

HCID 89733627HCID 89733627, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-ethyl-1-isothiocyanato-4-methoxybenzene (4.9 g, 25 mmol) in ethanol (22 mL), was added slowly, hydrazine-hydrate (1.3 g, 28 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was evaporated under reduced pressure and diluted with ethyl acetate (250 mL) and washed with water (2×50 mL), followed by brine (2×50 mL). The organic phase was dried over sodium sulfate, filtered, and evaporated under reduced pressure. Purification by flash column chromatography using 0-40% ethyl acetate/hexanes as eluent provided the title compound as a white solid (4.9 g, 86%): mp 113-115° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.19 (s, 1H), 8.89 (s, 1H), 7.20-7.19 (m, 1H), 6.77-6.71 (m, 2H), 4.71 (bs, 2H), 3.74 (s, 3H), 2.52-2.47 (m, 2H), 1.13-1.08 (m, 3H); ESIMS m/z 224 ([M−H]−).

Aufarbeitung

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additiondiluted with ethyl acetate (250 mL)
  3. washwashed with water (2×50 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7d086552569740adaeb2437329c0ff14
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029560B2

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