1H-1,2,4-Triazole → HCID 23039725, compound

HRID 2166413Notes

Reaction equation

HRID 2166413 reaction equation
S([O-])(=O)(=O)C.CS(O[CH2:11][C:12]([O:24][CH2:25][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:28]1[CH:32]=[N:31][CH:30]=[N:29]1>CO>[N:28]1([CH2:11][C:12]([O:24][CH2:25][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:32]=[N:31][CH:30]=[N:29]1

Participants

6

Reactant 4

HCID 92571H-1,2,4-Triazole2×HCID 85257MethanesulfonateHCID 5360545Sodium2×HCID 23039727HCID 23039727, compound

Product 1

HCID 23039725HCID 23039725, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

The mesylate prepared in accordance with (a) is reacted with the sodium salt of 1,2,4-triazole. This is effected by dissolving 0.83 g of sodium in 30 ml of methanol, adding 2.5 g of 1,2,4-triazole and removing the solvent in vacuo. A solution of 8.55 g of the mesylate in 30 ml of dimethyl sulfoxide is added to the residual sodium salt. After being heated for 5 hours on a bath at 120° C., the mixture is cooled to room temperature and extracted with diethyl ether. The combined extracts are washed with water, dried over sodium sulfate and concentrated in vacuo. Yield of crude product 7.6 g. The crude product is purified by column chromatography (silica gel; 1:4 ethyl acetate/petroleum ether) and affords a colourless oil, which crystallises after a few days. Recrystallisation from 16 ml of petroleum ether gives 3.7 g of the end product. Melting point 67° C. 100 MHz-1H-NMR (CDCl3): δ=7.63 and 7.72 ppm (s, 2H of triazole); 7.0-7.4 ppm (m, 3H, aromatic); 4.8 ppm (m, 2H, --CH2N); 3.2-3.8 ppm (m, 2H, --OCH2 --CH3); 1.7-2.4 ppm (m, 2H, --CH2CH2CH3); 1.3 ppm (t, 3H, --OCH2CH3); 0.7-1.4 ppm (m, 5H, --CH2CH2CH3).

Workup

  1. customremoving the solvent in vacuo
  2. additionA solution of 8.55 g of the mesylate in 30 ml of dimethyl sulfoxide is added to the residual sodium salt
  3. temperaturethe mixture is cooled to room temperature
  4. extractionextracted with diethyl ether
  5. washThe combined extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by column chromatography (silica gel; 1:4 ethyl acetate/petroleum ether)
  9. customaffords a colourless oil, which
  10. customcrystallises after a few days
  11. customRecrystallisation from 16 ml of petroleum ether

Sources & evidence

ORD record
ord-f1c1c9340a824b388f3bae5f1ca5112f
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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