Potassium Carbonate → Dimethyl 1-(2-ethoxyethyl)-4-nitro-1H-pyrazole-3,5-dicarboxylate

HRID 2099301Notes

Reaction equation

HRID 2099301 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][CH2:10][CH2:11]Br)[CH3:8].[N+:13]([C:16]1[C:17]([C:25]([O:27][CH3:28])=[O:26])=[N:18][NH:19][C:20]=1[C:21]([O:23][CH3:24])=[O:22])([O-:15])=[O:14]>CN(C)C=O>[CH2:7]([O:9][CH2:10][CH2:11][N:18]1[C:17]([C:25]([O:27][CH3:28])=[O:26])=[C:16]([N+:13]([O-:15])=[O:14])[C:20]([C:21]([O:23][CH3:24])=[O:22])=[N:19]1)[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 1421248dimethyl 4-nitro-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 57446145Dimethyl 1-(2-ethoxyethyl)-4-nitro-1H-pyrazole-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.32 g, 9.57 mmol) and 2-ethoxyethyl bromide (1.18 mL, 9.57 mmol) were added to a solution of dimethyl 4-nitro-1H-pyrazole-3,5-dicarboxylate (EP 1241170, pg. 50, preparation 10) (2 g, 9.57 mmol) in N,N-dimethylformamide (35 mL) and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (200 mL) and water (100 mL). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 100:0 to 70:30 in 10% increments to yield the title product, 1.63 g.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate (200 mL) and water (100 mL)
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 100:0 to 70:30 in 10% increments

Sources & evidence

ORD record
ord-373a90d5c87749ec83974f8f339fdb77
Source dataset
uspto-grants-2009_08
Patent number
US07569572B2

Reaction notes

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