Acetyl chloride → HCID 13051756, compound

HRID 1447463Notes

Reaction equation

HRID 1447463 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]([Cl:22])([Cl:21])[CH:7]([OH:20])[CH:8]([N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)[C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]>CN(C)C=O>[Cl:22][C:6]([Cl:5])([Cl:21])[CH:7]([O:20][C:1](=[O:3])[CH3:2])[CH:8]([N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)[C:9](=[O:14])[C:10]([CH3:12])([CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 12902576HCID 12902576, compound

Product 1

HCID 13051756HCID 13051756, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.0 g (0.1 mol) of acetyl chloride were added to 31.5 g (0.1 mol) of 1,1,1-trichloro-2-hydroxy-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-hexan-4-one in 100 ml of dimethylformamide at room temperature. Thereafter, the mixture was heated under reflux for 4 hours. It was left to cool and concentrated by distilling off the solvent in vacuo. The residue was taken up in methylene chloride and the methylene chloride solution was washed with aqueous sodium bicarbonate solution and dried over sodium sulphate. The solvent was distilled off and the residue was taken up in 100 ml of diisopropyl ether. After the diisopropyl ether mixture had stood for several hours, colorless crystals precipitated. 14.3 g (40% of theory) of 1,1,1-trichloro-2-acetoxy-3-(1,2,4-triazol-1-yl)-5,5-dimethylhexan-4-one were obtained as the pure diastereomer of the A* form of melting point 128°-130° C.

Workup

  1. temperatureThereafter, the mixture was heated
  2. temperatureunder reflux for 4 hours
  3. waitIt was left
  4. temperatureto cool
  5. concentrationconcentrated
  6. distillationby distilling off the solvent in vacuo
  7. washthe methylene chloride solution was washed with aqueous sodium bicarbonate solution
  8. dry with materialdried over sodium sulphate
  9. distillationThe solvent was distilled off
  10. waitAfter the diisopropyl ether mixture had stood for several hours
  11. customcolorless crystals precipitated

Sources & evidence

ORD record
ord-be23384b511a4263b01c4cedefac172a
Source dataset
uspto-grants-1982_02
Patent number
US04316932

Reaction notes

Loading…