Reaction equation
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]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- additionwere added
- customThe solvent was removed under reduced pressure and water (10 mL)
- additionwere added
- extractionThe aq. layer was extracted with EA (10 mL)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the residue by FC (10:1 to 2:1 hept-EA)
Sources & evidence
- ORD record
- ord-4c19350b35c8489dbebb8f711c6e2315
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288419B2
Linked notes
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