Dimethyl Sulfoxide → HCID 19738036, compound

HRID 2255389Notes

Reaction equation

HRID 2255389 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:10]#[N:11].Cl[CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1.CS(C)=O.[OH-].[Na+]>O>[C:10]([C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH2:20][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)#[N:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 37438821-Chloromethyl-1H-1,2,4-triazoleHCID 19738020HCID 19738020, compound

Product 1

HCID 19738036HCID 19738036, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask was added 5.0 g. (0.021 mole) of 2-(2-methoxyphenyl)-3-(2-pyridyl)propionitrile, 5.0 g. (0.031 mole) of 1-(chloromethyl)-1,2,4-triazole, and 150 ml. of DMSO, followed by 10 g. (0.125 mole) of 50% aqueous sodium hydroxide over 30 minutes. The reaction exothermed to 40° C. and was stirred for an additional two hours. After cooling, water was added and the organic material extracted with ether. The combined ether extracts were then washed with water, dried using magnesium sulfate, filtered, and the ether removed by rotary evaporation to obtain 3.0 g. of organic residue which was recrystallized from ether yielding 1.3 g. of the product as a grey solid, melting point 155°-158° C.

Workup

  1. additionTo a flask was added 5.0 g
  2. customexothermed to 40° C.
  3. temperatureAfter cooling
  4. extractionthe organic material extracted with ether
  5. washThe combined ether extracts were then washed with water
  6. customdried
  7. filtrationfiltered
  8. customthe ether removed by rotary evaporation
  9. customto obtain 3.0 g
  10. customof organic residue which was recrystallized from ether yielding 1.3 g

Sources & evidence

ORD record
ord-354e1412b22d4d1789552759219b2b12
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

Loading…