Ethyl bromopyruvate → 3-(2-Nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester

HRID 1667008

Reaktionsgleichung

Reaktionsgleichung von HRID 1667008
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1)([O-:3])=[O:2].Br[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(C(C)=O)C>[CH2:22]([O:21][C:19]([C:18]1[N:15]=[C:12]2[N:11]([CH:17]=1)[C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[CH:14][S:13]2)=[O:20])[CH3:23]

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvate2×HCID 5957794-(2-Nitrophenyl)thiazole-2-amine

Produkt 1

HCID 596802093-(2-Nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl esterAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

4-(2-Nitro-phenyl)-thiazol-2-ylamine (1.60 g, 7.2 mmol) was mixed with 50 mL of methyl ethyl ketone along 0.90 mL of ethyl bromopyruvate (7.2 mmol) and stirred under reflux for 24 hours. Another equivalent of ethyl bromopyruvate (0.90 mL, 7.2 mmol) was added and the reaction mixture was stirred under reflux for another 8 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 5% MeOH) to afford 1.2 g of 3-(2-nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester (52% yield).

Aufarbeitung

  1. temperatureunder reflux for 24 hours
  2. stirringthe reaction mixture was stirred
  3. temperatureunder reflux for another 8 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (Isco, gradient elution, CH2Cl2 to 95% CH2Cl2, 5% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-c896240064c74f03abb48a8a0d0aa40f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044198B2

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