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

HRID 861589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861589
[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.;

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-f95e3545deb14d72a6da2df27e095848
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714503

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