N-Iodosuccinimide → HCID 178432598, compound

HRID 1488033Notes

Reaction equation

HRID 1488033 reaction equation
C1C(=O)N([I:8])C(=O)C1.[CH3:9][C:10]1[N:11]=[C:12]([C:15]2([CH3:19])[CH2:18][O:17][CH2:16]2)[NH:13][CH:14]=1>C(#N)C>[I:8][C:14]1[NH:13][C:12]([C:15]2([CH3:19])[CH2:16][O:17][CH2:18]2)=[N:11][C:10]=1[CH3:9]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178430849HCID 178430849, compound2×

Product 1

HCID 178432598HCID 178432598, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NIS (2.61 g, 11.58 mmol) was added portion-wise to a solution of 4-methyl-2-(3-methyloxetan-3-yl)-1H-imidazole (compound 175.1, 1.76 g, 11.58 mmol) in acetonitrile (60 mL). The mixture was stirred at room temperature for 1 hour, then was partitioned between EtOAc (300 mL) and water (80 mL). The organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL), dried (MgSO4) and concentrated under reduced pressure to give the title compound as a light yellow solid (3.0 g, 93%). m/z (ES+) 279 (M+H)+.

Workup

  1. customwas partitioned between EtOAc (300 mL) and water (80 mL)
  2. washThe organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e71dc75488c42a486dd9af1e0e78679
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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