1H-1,2,4-Triazole → HCID 23039697, compound

HRID 2166411Notes

Reaction equation

HRID 2166411 reaction equation
CS(O[CH2:6][C:7]([O:19][CH3:20])([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])[CH2:8][CH2:9][CH3:10])(=O)=O.[Na].[NH:22]1[CH:26]=[N:25][CH:24]=[N:23]1>CS(C)=O>[N:22]1([CH2:6][C:7]([O:19][CH3:20])([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[CH2:8][CH2:9][CH3:10])[CH:26]=[N:25][CH:24]=[N:23]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 23039678HCID 23039678, compound

Product 1

HCID 23039697HCID 23039697, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The crude product prepared in (a) is dissolved in 50 ml of absolute dimethyl sulfoxide, and 2.2 g (24 mmoles) of the sodium salt of 1,2,4-triazole are added. The reaction mixture is stirred for 16 hours at a bath temperature of 120° C. The resulting dark solution is cooled to room temperature, poured into ice water and extracted twice with ethyl acetate. The combined extracts are washed four times with half-saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product is purified by colum chromatography (silica gel; 1:1 ethyl acetate/petroleum ether) and affords 3.2 g (=64% of theory) of a colourless oil. Boiling point 170°-175° C./0.04 mbar. 60 MHz-1H-NMR (CDCl3): δ=7.75 and 7.60 ppm (2s, 2H of the triazole); 6.9-7.5 ppm (m, 3H, aromatic); 4.8 ppm (4 lines AB spectrum, 2H, CH2N); 3.4 ppm (s, 3H, OCH3); 1.7-2.5 ##STR35## 0.7-1.5 ppm (m, 5H, CH2CH3).

Workup

  1. temperatureThe resulting dark solution is cooled to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts are washed four 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 colum chromatography (silica gel; 1:1 ethyl acetate/petroleum ether)
  8. customaffords 3.2 g (=64% of theory) of a colourless oil

Sources & evidence

ORD record
ord-3753b010fd3c45e8a35472deba98ded4
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

Loading…