Potassium Carbonate → 3-hepta fluoropropylsulfanyl-1-(3-methyl-4-nitrobenzyl)-5-trifluoromethyl-1H-(1,2,4)-triazole

HRID 2243247Notes

Reaction equation

HRID 2243247 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[F:13][C:14]([F:32])([C:28]([F:31])([F:30])[F:29])[C:15]([S:18][C:19]1[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[NH:21][N:20]=1)([F:17])[F:16].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(OCC)(=O)C>[F:32][C:14]([F:13])([C:28]([F:29])([F:30])[F:31])[C:15]([S:18][C:19]1[N:23]=[C:22]([C:24]([F:25])([F:27])[F:26])[N:21]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)[N:20]=1)([F:16])[F:17]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 86076326HCID 86076326, compound

Product 1

HCID 866171353-hepta fluoropropylsulfanyl-1-(3-methyl-4-nitrobenzyl)-5-trifluoromethyl-1H-(1,2,4)-triazoleYield 29.7%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-4-nitrobenzyl chloride (0.43 g), 3-heptafluoropropylsulfanyl-5-trifluoromethyl-1H-(1,2,4)-triazole (0.70 g), tetrabutylammonium iodide (0.09 g), 18-crown-6 (0.06 g) and potassium carbonate (0.48 g) were refluxed in acetonitrile (10 ml) for 2 hours. After cooling, the reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 3-heptafluoropropylsulfanyl-1-(3-methyl-4-nitrobenzyl)-5-trifluoromethyl-1H-(1,2,4)-triazole (0.30 g).

Workup

  1. temperatureAfter cooling
  2. washwashed with water and saturated aqueous solution of sodium chloride
  3. dry with materialAfter drying the organic layer with magnesium sulfate
  4. distillationthe solvent was distilled off under the reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e4b24470ae442d683e253023a19698d
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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