Ethyl Acetate → HCID 58083500, compound

HRID 1254001Notes

Reaction equation

HRID 1254001 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]([CH3:12])=[N:4]1)[CH3:2].[I:13]N1C(=O)CCC1=O.CCOC(C)=O>CN(C=O)C.O>[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([I:13])[C:5]([CH3:12])=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 22167575Methyl 1-ethyl-3-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 58083500HCID 58083500, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a flask, methyl 1-ethyl-3-methylpyrazol-5-ylcarboxylate (1.00 g, 0.006 mol, Ref. CN1626520A) was dissolved in 10 mL of DMF and N-iodosuccinimide (1.47 g, 0.007 mol) was added in batches. After reacting for 8 h at r.t., the mixture was diluted with 50 mL of water, and then extracted with 50 mL of ethyl acetate. The organic layer was washed with 50 mL of saturated aqueous sodium bicarbonate solution and 50 mL of saturated brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. Column chromatography (EtOAc:P.E.=1:10 as eluent) gave 0.82 g of the title compound as a yellow oil (yield 47%).

Workup

  1. extractionextracted with 50 mL of ethyl acetate
  2. washThe organic layer was washed with 50 mL of saturated aqueous sodium bicarbonate solution and 50 mL of saturated brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77e9f95127f54d5da99d175609078835
Source dataset
uspto-grants-2013_06
Patent number
US08455532B2

Reaction notes

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