Dimethyl Sulfoxide → 2-(2,4-Dichlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]butyramide

HRID 54905Notes

Reaction equation

HRID 54905 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH2:18][CH3:19])([CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[C:10]#[N:11].CS(C)=[O:22].O.[OH-].[Na+]>C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)([CH2:18][CH3:19])[C:10]([NH2:11])=[O:22]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 14798Sodium HydroxideHCID 54422114alpha-(2,4-dichlorophenyl)-alpha-ethyl-1H-1,2,4-triazole-1-propanenitrile

Product 1

HCID 199569642-(2,4-Dichlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]butyramideYield 79%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
91 °C

Procedure

To a 1 liter flask was charged 206.5 g (0.7 mole) of alpha-(2,4-dichlorophenyl)-alpha-ethyl-1H-1,2,4-triazole-1-propanenitrile and 500 mL of dimethyl sulfoxide and 200 mL of water. To the stirring solution was added 67.2 g (0.84 moles) of 50% sodium hydroxide. The reaction mixture was heated at 91° C. (steam bath) for 3 hours after which GLC indicated the starting material was consumed. The reaction was cooled to 30° C. then poured into water and extracted with ethyl acetate. After drying, the ethyl acetate was treated with charcoal and filtered through Celite®. Removal of the solvent gave a foamy oil which was stirred and diluted with ethyl acetate then treated with hexane until cloudy. Within 1 hour a solid formed which was cooled at 0° C. The product was filtered and washed with an ether and hexane mixture, then dried and provided 172 g (79% yield) of a white solid, melting point 164°-165° C.

Workup

  1. customwas consumed
  2. temperatureThe reaction was cooled to 30° C.
  3. additionthen poured into water
  4. extractionextracted with ethyl acetate
  5. customAfter drying
  6. additionthe ethyl acetate was treated with charcoal
  7. filtrationfiltered through Celite®
  8. customRemoval of the solvent
  9. customgave a foamy oil which
  10. customWithin 1 hour a solid formed which
  11. temperaturewas cooled at 0° C
  12. filtrationThe product was filtered
  13. washwashed with an ether and hexane mixture
  14. customdried

Sources & evidence

ORD record
ord-99ff43634bfa4e8ea434464e3dd2b697
Source dataset
uspto-grants-1997_04
Patent number
US05624916

Reaction notes

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