Water → HCID 13051756, compound

HRID 851685Notes

Reaction equation

HRID 851685 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[Cl:6][C:7]([Cl:23])([Cl:22])[CH:8](Cl)[CH:9]([N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12].O>C(O)(=O)C>[Cl:23][C:7]([Cl:6])([Cl:22])[CH:8]([O:3][C:1](=[O:4])[CH3:2])[CH:9]([N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10](=[O:15])[C:11]([CH3:13])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 12945122HCID 12945122, compound

Product 1

HCID 13051756HCID 13051756, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16.4 g (0.2 mol) of anhydrous sodium acetate were added to 31.5 g (0.1 mol) of 1,1,1,2-tetrachloro-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-hexan-4-one in 150 ml of glacial acetic acid. The mixture was stirred at room temperature overnight and then heated to 40° C. for about 4 hours. The reaction mixture was then added to 1,000 ml of water and extracted twice with 250 ml of chloroform each time. The combined organic phases were dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The solid residue was recrystallized from ethanol and rinsed with a little hexane. 27.8 g (77.8% of theory) of 1,1,1-trichloro-2-acetoxy-3-(1,2,4-triazol-1-yl)-5,5-dimethylhexan-4-one were obtained as a diastereomer mixture of melting point 115°-119° C.

Workup

  1. temperatureheated to 40° C. for about 4 hours
  2. extractionextracted twice with 250 ml of chloroform each time
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated
  5. distillationby distilling off the solvent in vacuo
  6. customThe solid residue was recrystallized from ethanol
  7. washrinsed with a little hexane

Sources & evidence

ORD record
ord-1f48a2b4f0fe410ab45373e4411010c8
Source dataset
uspto-grants-1983_05
Patent number
US04386088

Reaction notes

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