Hydrochloric Acid → HCID 23725857, compound

HRID 2219301Notes

Reaction equation

HRID 2219301 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][O:9][CH:10]=2)[N:3]=[CH:2]1.[CH3:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[C:11]1([C:7]2[C:6]([C:4]3[N:3]=[CH:2][N:1]([C:23]4[CH:24]=[CH:25][C:20]([C:18](=[O:19])[CH3:17])=[CH:21][CH:22]=4)[CH:5]=3)=[CH:10][O:9][N:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 178420174HCID 178420174, compound

Product 1

HCID 23725857HCID 23725857, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(1H-imidazol-4-yl)-3-phenyl-isoxazole (106 mg, 0.5 mmol) in DMF (2.5 mL) was added 4-fluoroacetophenone (61 mL, 0.5 mmol) and potassium carbonate (138 mg, 1.0 mmol) and the resulting mixture heated at 120° C. overnight. The resulting mixture was then poured into HCl (1 N, 200 mL) and extracted with ethyl acetate which was then washed with brine, dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 0:100) afforded the title compound (36 mg, 22%) which was obtained as a light yellow solid. MS: m/e=330.1 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate which
  2. washwas then washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 0:100)

Sources & evidence

ORD record
ord-9a3813aa0ca54073b934ca0d40c16eaa
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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