2-Aminothiazole → Thiourea, N-(3-phenylpropyl)-N'-2-thiazolyl-

HRID 233676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 233676
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]=[C:11]=[S:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1.C(OCC)(=O)C>CN(C)C=O>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)=[S:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 21552-AminothiazoleHCID 8857Ethyl AcetateHCID 758153-Phenylpropyl isothiocyanate

Produkt 1

HCID 3001100Thiourea, N-(3-phenylpropyl)-N'-2-thiazolyl-Ausbeute 16,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-phenylpropyl isothiocyanate (500 mg, 2.82 mmol) and 2-aminothiazole (300 mg, 3.0 mmol) in N,N-dimethylformamide (10 mL) was heated to 100° C. After 20 h, the reaction was cooled to room temperature and poured into ethyl acetate. The organic phase was washed with 1N hydrochloric acid, water (3×), and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The solid obtained was purified by flash chromatography on silica gel (1% ethyl acetate in dichloromethane) and then recrystallized from ethyl acetate to provide 129 mg of the title product. A second crop was recrystallized from 1:1 ethyl acetate/hexanes to provide another 110 mg of the title product. Total yield of the title product: 239 mg (30%) as an off-white solid. A sample was recrystallized again from ethyl acetate:

Aufarbeitung

  1. washThe organic phase was washed with 1N hydrochloric acid, water (3×), 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 flash chromatography on silica gel (1% ethyl acetate in dichloromethane)
  7. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9da61bc4048e4d7ea142ae175a9d7d4c
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593993

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