Imidazole → HCID 22165707, compound

HRID 1032466Notes

Reaction equation

HRID 1032466 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:17])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:5][CH:4]=1.[I-].C[S+](C)(C)=O.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1.[C:31](=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C>[N:26]1([CH2:31][C:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:4][CH:5]=2)([OH:17])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 22165695HCID 22165695, compound

Product 1

HCID 22165707HCID 22165707, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1-(4-trifluoromethylphenyl)-3-(1,2,4,-triazol-1-yl)propan-2-one (1.5 g), trimethylsulphoxonium iodide (1.5 g), imidazole (0.46 g), potassium carbonate (0.75 g) in tert-butyl alcohol (20 ml) was heated at φ° for 3 h. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer was separated, washed with water and then brine, and dried. The dried extract was evaporated to dryness under reduced pressure, and the residue was purified by chromatography on silica, using 5% by volume methanol in chloroform as eluent. After evaporation of the solvent, the residue crystallised from a mixture of ethyl acetate and hexane to give 3-(imidazol-1-yl)1-(1,2,4-triazol-1-yl)-2(4-trifluoromethylbenzyl)-propan-2-ol, m.p. 154-155°C. (Example 30). In a similar manner there were prepared 2-(4-chlorobenzyl)-3-(imidazol-1yl)-1-(1,2,4-triazol-1-yl) propan-2-ol, m.p. 159-161° (Example 31) and 1,3-di(imidazol-1yl)-2-(4-trifluoromethylbenzyl)propan-2-ol, m.p. 177-178° (Example 32). ##STR1##

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialbrine, and dried
  5. extractionThe dried extract
  6. customwas evaporated to dryness under reduced pressure
  7. customthe residue was purified by chromatography on silica
  8. customAfter evaporation of the solvent
  9. customthe residue crystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ac85b2a3559843218cc4b8e133619076
Source dataset
uspto-grants-1990_09
Patent number
US04957934

Reaction notes

Loading…