1H-1,2,4-Triazole → HCID 13457303, compound

HRID 463016Notes

Reaction equation

HRID 463016 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[I-].C[S+](C)(C)=O.[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1.[C:25](=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.ClC(Cl)(Cl)C.[OH-].[Na+].CN(C)C=O.O.C(OCC)(=O)C>[Cl:11][C:8]1[CH:7]=[CH:6][C:5]([C:3]([OH:4])([C:2]([F:1])([F:12])[F:13])[CH2:25][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)=[CH:10][CH:9]=1

Participants

11

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 67578Ethanone, 1-(4-chlorophenyl)-2,2,2-trifluoro-HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

HCID 13457303HCID 13457303, compoundYield 9.3%

Reagents, catalysts & solvents 6

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 62781,1,1-TrichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

2,2,2-Trifluoro-4'-chloroacetophenone (0.8 g, 3.84 mmole), trimethylsulphoxonium iodide (1.02 g, 4.6 mmole) and cetyltrimethylammonium bromide (0.1 g, 0.27 mmole) were stirred in a mixture of 1,1,1-trichloroethane (40 ml) and 18% sodium hydroxide solution (20 ml) at 75° for 2 hours. The mixture was then allowed to cool, the organic layer was separated, evaporated, and the residue was stirred in dimethylformamide (50 ml) with 1,2,4-triazole (1 g, 14.5 mmole) and anhydrous potassium carbonate (2 g, 14.5 mmole) at 90° for 4 hours. The mixture was then allowed to cool, ethyl acetate (100 ml) and water (50 ml) were added and the aqueous layer was separated. The organic layer was washed a further 6 times with water (200 ml in total), dried over magnesium sulphate, and evaporated to give a gum (104 mg) which was chromatographed on silica (230-400 mesh), eluting with ethyl acetate to give as a colorless solid the title compound, 84 mg (8%). One recrystallization from dichloromethane/hexane gave colorless crystals, 64 mg, m.p. 117°-118° C.

Workup

  1. temperatureto cool
  2. customthe organic layer was separated
  3. customevaporated
  4. temperatureto cool
  5. customthe aqueous layer was separated
  6. washThe organic layer was washed a further 6 times with water (200 ml in total)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-d563bd618a284d32a7c92aabc1cd4e32
Source dataset
uspto-grants-1985_05
Patent number
US04518604

Reaction notes

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