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

HRID 855601Notes

Reaction equation

HRID 855601 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([C:13]([O:15][CH3:16])=[O:14])[NH:7][N:6]=1)=[O:4].[CH2:17]([O:19][CH2:20][CH2:21]Br)[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([O:19][CH2:20][CH2:21][N:6]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:9]([N+:10]([O-:12])=[O:11])[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:7]1)[CH3:18]

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

4-Nitro-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester (2.0 g, 8.83 mmol) was added to a solution of 2-ethoxyethyl bromide (1.18 mL, 10.45 mmol) and potassium carbonate (1.32 g, 9.56 mmol) in N,N-dimethylformamide (35 mL) and the reaction mixture stirred for 48 hours at room temperature. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate (200 mL) and water (100 mL). The organic layer was separated, 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 to yield the title product, 1.63 g.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate (200 mL) and water (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel eluting with pentane:ethyl acetate 100:0 to 70:30

Sources & evidence

ORD record
ord-7a7354618de7402192c890a05053a0c8
Source dataset
uspto-grants-2007_08
Patent number
US07262192B2

Reaction notes

Loading…