Triethylamine → N-benzyl-2-(N'-hydroxycarbamimidoyl)-4-methylthiazole-5-carboxamide

HRID 2381798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381798
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]#[N:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C(N(CC)CC)C>C(O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16](=[N:20][OH:21])[NH2:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 68492000N-benzyl-2-cyano-4-methylthiazole-5-carboxamide

Produkt 1

HCID 136404881N-benzyl-2-(N'-hydroxycarbamimidoyl)-4-methylthiazole-5-carboxamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of N-benzyl-2-cyano-4-methylthiazole-5-carboxamide (0.15 g, 0.58 mmol) and hydroxylamine hydrochloride (0.09 g, 1.28 mmol) in ethanol (7 mL) was added triethylamine (0.2 mL, 1.43 mmol). The reaction mixture was heated to reflux for 3 hour, cooled to ambient temperature and concentrated in vacuo. The solid was washed with water and dried to afford the title compound in 70% yield (0.12 g): 1H NMR (300 MHz, CDCl3) δ 7.43-7.18 (m, 5H), 6.42 (br s, 1H), 5.74 (br s, 2H), 4.54 (d, J=5.3 Hz, 2H), 2.63 (s, 3H); MS (ES+) m/z 291.1 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hour
  3. concentrationconcentrated in vacuo
  4. washThe solid was washed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fb68ef30740b4b08aa7fad777cde5f4f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258160B2

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