1H-1,2,4-Triazole → 1-(1H-1,2,4-triazol-1-yl)-2-isopropoxy-2-(2,4-dichlorophenyl)pentane

HRID 2166414Notes

Reaction equation

HRID 2166414 reaction equation
S([O-])(=O)(=O)C.CS(O[CH2:11][C:12]([O:24][CH:25]([CH3:27])[CH3:26])([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[CH2:13][CH2:14][CH3:15])(=O)=O.[Na].[NH:29]1[CH:33]=[N:32][CH:31]=[N:30]1>CS(C)=O>[N:29]1([CH2:11][C:12]([O:24][CH:25]([CH3:27])[CH3:26])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[CH2:13][CH2:14][CH3:15])[CH:33]=[N:32][CH:31]=[N:30]1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 85257MethanesulfonateHCID 5360545SodiumHCID 230396911-(Methylsulfonyloxy)-2-isopropoxy-2-(2,4-dichlorophenyl)-pentane

Product 1

HCID 230396861-(1H-1,2,4-triazol-1-yl)-2-isopropoxy-2-(2,4-dichlorophenyl)pentane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The mesylate prepared in accordance with (a) is dissolved in 100 ml of absolute dimethyl sulfoxide, and 3.2 g (35 mmoles) of the sodium salt of 1,2,4-triazole are added. The reaction mixture is stirred for 8 hours at a bath temperature of 120° C. and is then cooled to room temperature and poured into ice water, and the mixture is extracted twice with ethyl acetate. The combined extracts are washed 4 times with half-saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product is purified by column chromatography (silica gel; 1:1 ethyl acetate/petroleum ether) and affords a colourless oil. n50D =1.5299. 100 MHz -1H-NMR (CDCl3): δ=7.75 and 7.65 ppm (s, 2H of triazole); 7.1-7.6 ppm (m, 2H, aromatic); 4.85 ppm (dd, 2H, CH2 -N); 4.0 ppm (m, 1H, --CH(CH3)2); 0.8-2.6 ppm (m, 14H, --CH(CH3)2, --CH2 --CH2 --CH3);

Workup

  1. temperatureis then cooled to room temperature
  2. extractionthe mixture is extracted twice with ethyl acetate
  3. washThe combined extracts are washed 4 times with half-saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography (silica gel; 1:1 ethyl acetate/petroleum ether)
  8. customaffords a colourless oil

Sources & evidence

ORD record
ord-e5341c479bf640c097cfdb5bb78ac6ec
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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