N-Iodosuccinimide → HCID 178470248, compound

HRID 1488128Notes

Reaction equation

HRID 1488128 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:5][CH:6]=1.C1C(=O)N([I:19])C(=O)C1>CC#N>[I:19][C:6]1[NH:5][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178470250HCID 178470250, compound2×

Product 1

HCID 178470248HCID 178470248, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of ethyl 4-methyl-1H-imidazole-2-carboxylate (compound 239.1, 100 mg, 0.65 mmol) in CH3CN (10 mL). NIS (218 mg, 0.97 mmol) was added to the reaction. The reaction mixture was stirred for overnight at room temperature, then concentrated under reduced pressure. The residue was dissolved with 30 mL of EtOAc, then was washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 80 mg (44%) of the title compound as a yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved with 30 mL of EtOAc
  4. washwas washed with 2×20 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd9806ebd1c74493b30c9f635a0a13ee
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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