Reaktion #71103

Reaktionsgleichung

DIPEA

N2

5-chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

4-nitro-2H-[1,2,3]triazole

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title compound

2-[2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-5-ylmethyl]-4-nitro-2H-[1,2,3]triazole

Lösungsmittel

EA

Water

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   ExtraktionThe aq. layer was extracted with EA (10 mL)
3. 3
   Trocknenextracts were dried over NaSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvents were removed under reduced pressure
6. 6
   SonstigePurification of the residue by FC (5:1 to 2:1 hept-EA)

Vorschrift

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 (339 mg, 1.54 mmol) in DMF (2.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (160 mg, 1.40 mmol) in DMF (2.0 mL) pre-treated for 30 min with DIPEA (0.48 mL, 2.81 mmol) and the reaction mixture was stirred for 72 h at 50° C. 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 NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (5:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (1:2 hept-EA)=0.39. LC-MS-conditions 02: tR=0.89 min; [M+H]+=298.13.

Quelle