Hydrochloric Acid → 1-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-thiazol-4-yl]-ethanone

HRID 2040031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040031
N#N.[CH3:3][C:4]1([C:9]2[N:10]=[C:11]([CH2:14][N:15]3[N:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[N:16]3)[S:12][CH:13]=2)OCC[O:5]1.Cl.[OH-].[Na+]>C1COCC1>[N+:20]([C:18]1[CH:17]=[N:16][N:15]([CH2:14][C:11]2[S:12][CH:13]=[C:9]([C:4](=[O:5])[CH3:3])[N:10]=2)[N:19]=1)([O-:22])=[O:21]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14798Sodium HydroxideHCID 671276452-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

Produkt 1

HCID 671276681-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-thiazol-4-yl]-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole (2.360 g, 7.94 mmol) in THF (40.0 mL) was treated with 1N HCl (21.4 mL, 21.4 mmol) and the reaction mixture was stirred at rt overnight. The reaction mixture was neutralized with 1N NaOH. The aq. layer was extracted twice with EA (20 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 (6:4 hept-EA) gave the title compound as a yellow solid: TLC:rf (6:4 hept-EA)=0.29. LC-MS-conditions 02: tR=0.81 min, [M+H]+=254.35.

Aufarbeitung

  1. extractionThe aq. layer was extracted twice with EA (20 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (6:4 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-f01c301eeb044b92aea03647e5233467
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580831B2

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