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

HRID 2065038

Reaktionsgleichung

Reaktionsgleichung von HRID 2065038
N#N.Cl[CH2:4][C:5]1[N:6]=[C:7]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[S:8][CH:9]=1.[N+:16]([C:19]1[NH:23][N:22]=[CH:21][CH:20]=1)([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].[Br-]>CC(C)=O.CC(=O)OCC.O>[CH3:15][C:10]1([C:7]2[S:8][CH:9]=[C:5]([CH2:4][N:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[N:23]3)[N:6]=2)[O:14][CH2:13][CH2:12][O:11]1

Komponenten

9

Edukt 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 1234193-NitropyrazoleHCID 669288134-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

Produkt 1

HCID 669292022-(2-Methyl-[1,3]dioxolan-2-yl)-4-(3-nitro-pyrazol-1-ylmethyl)-thiazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittel2×HCID 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-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole (174 mg, 0.79 mmol) in acetone (2.0 mL) was added to a solution of 5-nitro-1H-pyrazole (90 mg, 0.79 mmol) in acetone (2.0 mL). K2CO3 (330 mg, 2.38 mmol) followed by TBA bromide (51 mg, 0.16 mmol) were added and the reaction mixture was stirred at rt overnight. Water (10 mL) and 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 (1:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:1 hept-EA)=0.29. LC-MS-conditions 02: tR=0.89 min, [M+H]+=297.23.

Aufarbeitung

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (10 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 (1:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-847dc52d889d4f81ac88a42543f6fa0e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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