Methyl iodide → HCID 67106400, compound

HRID 1910801Notes

Reaction equation

HRID 1910801 reaction equation
[CH:1]([C:4]1[NH:5][CH:6]=[C:7]([C:9]([CH3:20])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH3:10])[N:8]=1)([CH3:3])[CH3:2].[C:21](=O)([O-])[O-].[K+].[K+].IC>C1COCC1>[CH:1]([C:4]1[N:5]([CH3:21])[CH:6]=[C:7]([C:9]([CH3:10])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH3:20])[N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178440051HCID 178440051, compound

Product 1

HCID 67106400HCID 67106400, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-isopropyl-4-[1-methyl-1-(3-nitro-phenyl)-ethyl]-1H-imidazole (0.35 g, 1.28 mmol) in THF (2 mL) was added potassium carbonate (0.21 g, 1.5 mmol) and iodomethane (0.12 mL, 1.92 mmol). The mixture was heated at 50° C. for 5 h then concentrated in vacuo. The residue was partitioned between water and DCM then the organic phase was dried over sodium sulfate and evaporated to afford 2-isopropyl-1-methyl-4-[1-methyl-1-(3-nitro-phenyl)-ethyl]-1H-imidazole (0.2 g, 56%) as colourless semisolid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between water and DCM
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-84b15c6466d54d7297ce82ce2d45c1ca
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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