N-Iodosuccinimide → HCID 90029656, compound

HRID 1488163Notes

Reaction equation

HRID 1488163 reaction equation
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][NH:5][CH:6]=1.C1C(=O)N([I:19])C(=O)C1>CN(C)C=O>[I:19][C:6]1[NH:5][N:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178470484HCID 178470484, compound

Product 1

HCID 90029656HCID 90029656, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Into a 250-mL round-bottom flask, was placed a solution of ethyl 4-methyl-1H-pyrazole-3-carboxylate (600 mg, 3.89 mmol) in N,N-dimethylformamide (20 mL). NIS (2.2 g, 9.78 mmol) was added and the resulting mixture was stirred for 6 h at 50° C., then quenched with water (10 mL). The mixture was extracted with ethyl acetate (3×40 mL) and the combined organic extracts were washed with aqueous Na2S2O3 (sat., 2×30 mL) and brine (2×20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (1:10) as eluent to obtain the title compound as a white solid (800 mg, 73%).

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. customquenched with water (10 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×40 mL)
  4. washthe combined organic extracts were washed with aqueous Na2S2O3 (sat., 2×30 mL) and brine (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (1:10) as eluent

Sources & evidence

ORD record
ord-ca8acbca2c744235a105fe13dd516249
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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