Diethyl Ether → 2-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062673
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(OCC)C>O1CCCC1>[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

5

Edukt 3

HCID 3283Diethyl EtherHCID 2723790ThioureaHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

Produkt 1

HCID 222824852-Amino-4-(3-cyanophenyl)-5-carboethoxythiazoleAusbeute 102,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (4.0 g, 13.5 mmol) in 100 mL of tetrahydrofuran was added thiourea (1.03 g, 13.5 mmol). The resulting mixture was stirred at 65° C. for 16 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was triturated with ether, taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with ethyl ether left the title compound as an off-white solid (3.79 g, 98%).

Aufarbeitung

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was triturated with ether
  4. washwashed with saturated aq Na2CO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a solid

Quellen und Nachweise

ORD-Eintrag
ord-d19b10cfcc5e4f20aba60ec8af47cc49
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962935B2

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