Bromide ion → 4-(4-Nitro-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

HRID 2065020

Reaktionsgleichung

Reaktionsgleichung von HRID 2065020
N#N.[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13]Cl)[N:12]=1)=[O:7])[CH3:4].C([O-])([O-])=O.[K+].[K+].[N+:21]([C:24]1[CH:25]=[N:26][NH:27][CH:28]=1)([O-:23])=[O:22].[Br-]>CC(C)=O.CC(=O)OCC.O>[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][N:26]2[CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]2)[N:12]=1)=[O:7])[CH3:4]

Komponenten

9

Edukt 5

HCID 259Bromide ionHCID 947Nitrogen2×HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 10822129Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

Produkt 1

HCID 669288954-(4-Nitro-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-chloromethyl-thiazole-2-carboxylic acid ethyl ester (1.84 g, 8.93 mmol) in acetone (20.0 mL) was treated, under inert atmosphere (N2) with K2CO3 (6.23 g, 44.66 mmol) followed by 4-nitro-1H-pyrazole (1.00 g, 8.93 mmol) and TBA bromide (576 mg, 1.79 mmol). The resulting mixture was stirred at rt overnight. Water (40 mL), followed by EA (50 mL) were added. The aq. layer was extracted with EA (50 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a yellow oil. TLC: rf (50:50 hept-EA)=0.30. LC-MS-conditions 02: tR=0.90 min; [M+H]+=283.25.

Aufarbeitung

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (50 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (50:50 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-385828603fc9419ea257798b5641aaa9
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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