1H-1,2,4-Triazole → HCID 14721529, compound

HRID 2372039Notes

Reaction equation

HRID 2372039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2([C:13]3([CH3:21])[CH2:16][C:15]([F:18])([F:17])[C:14]3([F:20])[Cl:19])[CH2:12][O:11]2)=[CH:4][CH:3]=1.[NH:22]1[CH:26]=[N:25][CH:24]=[N:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([C:13]2([CH3:21])[CH2:16][C:15]([F:18])([F:17])[C:14]2([F:20])[Cl:19])([OH:11])[CH2:12][N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 14721528HCID 14721528, compound

Product 1

HCID 14721529HCID 14721529, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

31.8 g of 2-[2-(4-chlorophenyl)-ethin-1-yl]-2-(2,3,3-trifluoro-2-chloro-1-methylcyclobut-1-yl)-oxirane are added at room temperature to a stirred mixture of 6.4 g of 1,2,4-triazole, 12.6 g of ground potassium carbonate and 300 ml of acetonitrile. The reaction mixture is refluxed for 12 hours, and then cooled and filtered. The filtrate is concentrated under reduced pressure, and the remaining residue is purified by column chromatography (ethyl acetate) on silica gel. 29 g (75.5% of theory) of 1-(4-chlorophenyl)-3-(2,3,3-trifluoro-2-chloro-1-methyl-cyclobut-1-yl)-4-(1,2,4-triazol-1-yl)-but-1-in-3-ol are obtained in form of a viscous oil.

Workup

  1. temperatureThe reaction mixture is refluxed for 12 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe remaining residue is purified by column chromatography (ethyl acetate) on silica gel

Sources & evidence

ORD record
ord-b0d844a48eed4b23b2ebcf2fe341b049
Source dataset
uspto-grants-1992_03
Patent number
US05097050

Reaction notes

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