1H-1,2,4-Triazole → HCID 23039722, compound

HRID 2166415Notes

Reaction equation

HRID 2166415 reaction equation
S([O-])(=O)(=O)C.CS(O[CH2:11][C:12]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH3:13])(=O)=O.[Na].[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1>CO.CS(C)=O.O>[N:27]1([CH2:11][C:12]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH3:13])[CH:31]=[N:30][CH:29]=[N:28]1

Participants

8

Reactant 4

HCID 92571H-1,2,4-Triazole2×HCID 85257MethanesulfonateHCID 5360545Sodium2×HCID 23039704HCID 23039704, compound

Product 1

HCID 23039722HCID 23039722, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
130 °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 0.52 g (23 mmoles) of sodium in 20 ml of absolute methanol, and adding 1.55 g (23 mmoles) of 1,2,4-triazole to this solution. The methanol is then removed in vacuo, and the mesylate prepared in (a) is added, dissolved in 20 ml of dimethyl sulfoxide, to the crystalline residue. The mixture is heated for 6.5 hours at a bath temperature of 130° C. and is allowed to cool to room temperature, water is added and the mixture is extracted with chloroform. The combined extracts are washed with half-saturated sodium chloride solution, dried over sodium sulfate and filtered, and the filtrate is concentrated in vacuo. The 3.74 g of crude product obtained are purified by column chromatography (silica gel; 1:1 ethyl acetate/petroleum ether) and afford 1.57 g of the pure end product in the form of an oil. 60 MHz-1H-NMR (CDCl3): δ=8.10 and 7.85 ppm (2s, 2H of triazole); 6.9-7.4 ppm (m, 4H, aromatic); 4.3 ppm (s, 2H, --CH2N); 2.9-3.4 ppm (m, 2H, OCH2); 1.2-1.7 ppm ##STR47## and OCH2CH2CH2CH3); 0.7-1.1 ppm (m, 3H, OCH2CH2CH2CH3).

Workup

  1. customThe methanol is then removed in vacuo
  2. customthe mesylate prepared in (a)
  3. additionis added
  4. temperatureto cool to room temperature
  5. extractionthe mixture is extracted with chloroform
  6. washThe combined extracts are washed with half-saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe 3.74 g of crude product obtained
  11. customare purified by column chromatography (silica gel; 1:1 ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-7ad7bc7e4bbb4b6f99727845889848a6
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

Loading…