Bromide ion → 5-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-carboxylic acid methyl ester

HRID 42738

Reaktionsgleichung

Reaktionsgleichung von HRID 42738
N#N.[N+:3]([C:6]1[CH:10]=[N:9][NH:8][N:7]=1)([O-:5])=[O:4].[CH3:11][O:12][C:13]([C:15]1[O:16][C:17]([CH2:20]Cl)=[CH:18][CH:19]=1)=[O:14].C([O-])([O-])=O.[K+].[K+].[Br-]>CC(C)=O>[CH3:11][O:12][C:13]([C:15]1[O:16][C:17]([CH2:20][N:8]2[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]2)=[CH:18][CH:19]=1)=[O:14]

Komponenten

7

Edukt 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 75065Methyl 5-(chloromethyl)-2-furoateHCID 2781504-nitro-2H-1,2,3-triazole

Produkt 1

HCID 673653265-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-nitro-2H-[1,2,3]triazole (1.50 g, 13.15 mmol) in acetone (26.3 mL) was treated with 5-chloromethyl-furan-2-carboxylic acid methyl ester (2.66 g, 14.47 mmol) followed by K2CO3 (9.18 g, 65.75 mmol) and TBA bromide (848 mg, 2.63 mmol). The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure, water (50 mL) was added and the product was extracted with EA (3×30 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)=0.22. LC-MS-conditions 02: tR=0.90 min.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure, water (50 mL)
  2. additionwas added
  3. extractionthe product was extracted with EA (3×30 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (50:50 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-6d0d94cd7f044357a20e66c2ebbc202e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536209B2

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