Isopropyl iodide → HCID 26793695, compound

HRID 1098593Notes

Reaction equation

HRID 1098593 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].I[CH:10]([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH:10]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178526856HCID 178526856, compound

Product 1

HCID 26793695HCID 26793695, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-nitroimidazole (0.500 g, 4.42 mmol), 2-iodopropane (0.553 ml, 5.53 mmol) and powdered K2CO3 (0.917 g, 6.63 mmol) were combined and stirred in DMF (25 ml) at 50° C. After 5 h, the reaction was cooled to RT. The reaction was diluted with EtOAc and filtered to remove inorganic salts, rinsing forward with EtOAc. The filtrate was evaporated to near dryness. The residue was diluted in EtOAc, washed with H2O (2×) and brine (1×), dried (MgSO4) and evaporated to afford 1-isopropyl-4-nitro-1H-imidazole (0.66 g, 96% yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 8.51 (s, 1H) 7.98 (s, 1H), 4.52-4.49 (m, 1H), 1.44 (d, 6H); MS (ESI) m/z: 156.0 (M+H+), 178.0 (M+Na+).

Workup

  1. filtrationfiltered
  2. customto remove inorganic salts
  3. washrinsing forward with EtOAc
  4. customThe filtrate was evaporated
  5. additionThe residue was diluted in EtOAc
  6. washwashed with H2O (2×) and brine (1×)
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-c0ef0a14f21440e8857a223d2d058cf0
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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