Bromide ion → 2-(2-Methyl-[1,3]dioxolan-2-yl)-5-(4-nitro-pyrazol-1-ylmethyl)-thiazole

HRID 2065053

Reaktionsgleichung

Reaktionsgleichung von HRID 2065053
N#N.Cl[CH2:4][C:5]1[S:9][C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)=[N:7][CH:6]=1.[N+:16]([C:19]1[CH:20]=[N:21][NH:22][CH:23]=1)([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].[Br-]>CC(C)=O>[CH3:15][C:10]1([C:8]2[S:9][C:5]([CH2:4][N:21]3[CH:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:23]=[N:22]3)=[CH:6][N:7]=2)[O:14][CH2:13][CH2:12][O:11]1

Komponenten

7

Edukt 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 669287935-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

Produkt 1

HCID 669287342-(2-Methyl-[1,3]dioxolan-2-yl)-5-(4-nitro-pyrazol-1-ylmethyl)-thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole (495 mg, 2.25 mmol) in acetone (1.0 mL) was added to a solution of 4-nitro-1H-pyrazole (268 mg, 2.37 mmol) in acetone (1.0 mL). K2CO3 (1.57 g, 11.27 mmol) followed by TBA bromide (145 mg, 0.45 mmol) were added and the reaction mixture was stirred at rt until completion. The solvent was removed under reduced pressure and water (10 mL) followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 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 (10:1 to 2:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (1:2 hept-EA)=0.24. LC-MS-conditions 01: tR=0.82 min, [M+H]+=296.93.

Aufarbeitung

  1. additionwere added
  2. customThe solvent was removed under reduced pressure and water (10 mL)
  3. additionwere added
  4. extractionThe aq. layer was extracted with EA (10 mL)
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (10:1 to 2:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-4c19350b35c8489dbebb8f711c6e2315
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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