Thiourea → 2-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062677
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C>[NH2:21][C:19]1[S:20][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=2)[N:18]=1

Komponenten

4

Edukt 2

HCID 2723790ThioureaHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

Produkt 1

HCID 222824852-Amino-4-(3-cyanophenyl)-5-carboethoxythiazoleAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (2.0 g, 6.75 mmol) in 100 mL of absolute ethanol was added thiourea (0.51 g, 6.75 mmol). The resulting mixture was stirred at 80° C. for 3 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with hexanes/ethyl ether left the title compound as an off-white solid (1.55 g, 65%). 1H NMR (DMSO-d6) δ: 8.03 (s, 1H); 7.93 (s, 2H) ; 7.91 (d, 1H); 7.82 (d, 1H); 7.58 (t, 1H); 4.05 (q, 2H); 1.10 (t, 3H).

Aufarbeitung

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. washwashed with saturated aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a solid

Quellen und Nachweise

ORD-Eintrag
ord-b93404e3693540fba539d7881408544d
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962935B2

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