N-[4-(4-Trifluoromethoxy-phenyl)-1H-imidazol-2-yl]-acetamide → 4-(4-Trifluoromethoxy-phenyl)-1H-imidazol-2-ylamine

HRID 1695201Notes

Reaction equation

HRID 1695201 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15]C(=O)C)[NH:13][CH:14]=2)=[CH:6][CH:5]=1>O.CO.S(=O)(=O)(O)O>[F:20][C:2]([F:1])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH2:15])[NH:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 178474425N-[4-(4-Trifluoromethoxy-phenyl)-1H-imidazol-2-yl]-acetamide

Product 1

HCID 1785083084-(4-Trifluoromethoxy-phenyl)-1H-imidazol-2-ylamineYield 98%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[4-(4-Trifluoromethoxy-phenyl)-1H-imidazol-2-yl]-acetamide (0.7 g, 2.6 mmol, 1.0 eq) was dissolved in water (18 mL) and methanol (18 mL), and 20 drops of sulfuric acid were added. The reaction was refluxed for 2 days, then the mixture was dried; the residue was diluted with water, the pH adjusted to 8 with NaOH 2N, the product was extracted with DCM and concentrated under reduced pressure to give 0.6 g of the title compound (yield 98%)

Workup

  1. temperatureThe reaction was refluxed for 2 days
  2. customthe mixture was dried
  3. additionthe residue was diluted with water
  4. extractionthe product was extracted with DCM
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63f449d3ec0e460b9e9d67a5313d2274
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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