Ethyl 2-aminothiazole-4-carboxylate → Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate

HRID 416611

Reaktionsgleichung

Reaktionsgleichung von HRID 416611
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])=O>C(C(C)=O)C>[CH2:10]([O:9][C:7]([C:5]1[N:6]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-:24])=[O:23])[N:1]=[C:2]2[S:3][CH:4]=1)=[O:8])[CH3:11]

Komponenten

4

Edukt 2

HCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 2440252-Bromo-2'-nitroacetophenone

Produkt 1

HCID 25232522Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylateAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

In a typical run, 2.1 g of ethyl 2-aminothiazole-4-carboxylate (Combi-Blocks, 0.0123 mol) was mixed with 25 mL of methyl ethyl ketone along with 2-bromo-2′-nitroacetophenone (3.0 g, 0.0123 mol). The reaction mixture was stirred under reflux for 18 hours. It was then cooled to room temperature and filtered to remove some of the solids. The filtrate was concentrated to afford 3.10 g of 6-(2-nitro-phenyl)-imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (MS, M++H=318).

Aufarbeitung

  1. temperatureunder reflux for 18 hours
  2. filtrationfiltered
  3. customto remove some of the solids
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-f11f0e9818664a20991016afb4914dc7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088928B2

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