Ethyl Acetate → N-(2-(1-Cyclohexenyl)ethyl)-N'-[2-pyridyl]thiourea

HRID 2257772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2257772
[C:1]1([CH2:7][CH2:8][N:9]=[C:10]=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(OCC)(=O)C>CN1CCCC1=O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 104392-AminopyridineHCID 27358811-(2-Isothiocyanatoethyl)cyclohex-1-ene

Produkt 1

HCID 3000476N-(2-(1-Cyclohexenyl)ethyl)-N'-[2-pyridyl]thioureaAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of 2-(1-cyclohexenyl)ethyl isothiocyanate (1.67 g, 10 mmol) and 2-aminopyridine (941 mg, 10 mmol) in N-methylpyrrolidinone (20 mL) was heated to 100° C. After 16.5 h, the reaction was cooled to room temperature and poured into ethyl acetate. The organic phase was washed with water (4×) and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The solid obtained was purified by recrystallization from ethyl acetate to provide 1.31 g of the titled product (50%) as a white crystalline solid: mp 153°-155° C.; IR (KBr, cm-1) 3219, 2921, 1605, 1569, 1537, 1481, 1319, 1235, 1181, 1092; 1H NMR (300 MHZ, DMSO-d6) δ 11.55 (s, 1H), 10.47 (s, 1H), 8.09 (d, J=3.9 Hz, 1H), 7.74-7.68 (m, 1H), 7.09 (d, J=8.3 Hz, 1H), 7.00-6.96 (m, 1H), 5.47 (s, 1H), 3.65-3.59 (m, 2H), 2.19 (t, J=6.6 Hz, 2H), 1.94-1.90 (m, 4H), 1.55-1.43 (m, 4H); MS (FD) m/e 261 (M+); UV (EtOH) 292 nm (ε=15926), 265 nm (ε=17724), 247 nm (ε=15198). Anal. Calcd for C14H19N3S: C, 64.33; H, 7.33; N, 16.08. Found: C, 64.12; H, 7.33; N, 15.89.

Aufarbeitung

  1. washThe organic phase was washed with water (4×) and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customwas purified by recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8498bf2518fc4b26abe0f9a17602c62a
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05658907

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