2-(3-fluoro-4-methyl-phenyl)-5-methyl-4-(2-methyl-2-nitro-propyl)-1H-imidazole → HCID 67031623, compound

HRID 2249610Notes

Reaction equation

HRID 2249610 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]([CH3:21])=[C:12]([CH2:14][C:15]([CH3:20])([N+:17]([O-])=O)[CH3:16])[N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]([CH3:21])=[C:12]([CH2:14][C:15]([NH2:17])([CH3:16])[CH3:20])[N:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 225635262-(3-fluoro-4-methyl-phenyl)-5-methyl-4-(2-methyl-2-nitro-propyl)-1H-imidazole

Product 1

HCID 67031623HCID 67031623, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(3-fluoro-4-methyl-phenyl)-5-methyl-4-(2-methyl-2-nitro-propyl)-1H-imidazole (1.6 g) in acetic acid (32 ml) was added in 2 equal portions of Zn dust (5.2 g) in 15 minutes at 20-25° C. The slightly exothermic reaction was stirred at RT for 1.5 h, the inorganic salts filtered off, and washed with acetic acid. The filtrate was concentrated almost to dryness, the residue quenched with cold conc. NaOH and brine, and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to dryness to obtain 2-[2-(3-fluoro-4-methyl-phenyl)-5-methyl-1H-imidazol-4-yl]-1,1-dimethyl-ethylamine (1.16 g) as a light yellow foam, pure enough to be used in the next step.

Workup

  1. customThe slightly exothermic reaction
  2. filtrationthe inorganic salts filtered off
  3. washwashed with acetic acid
  4. concentrationThe filtrate was concentrated almost to dryness
  5. customthe residue quenched with cold conc. NaOH and brine
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over magnesium sulphate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-6c3bd79fbacf4df0b81a9a31f69e1472
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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