1H-1,2,4-Triazole → HCID 23350019, compound

HRID 262452Notes

Reaction equation

HRID 262452 reaction equation
[C:1]([O:4][CH2:5][C:6]([CH3:20])([CH3:19])[C:7](=[O:18])[CH:8](Br)[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1.C(=O)([O-])[O-].[K+].[K+].O.O.O.O.O.O.O.O.[C:40]1([S:54]([OH:57])(=[O:56])=[O:55])[C:49]2[CH:48]=[CH:47][CH:46]=[C:45]([S:50]([OH:53])(=[O:52])=[O:51])[C:44]=2[CH:43]=[CH:42][CH:41]=1>CC(C)=O>[C:40]1([S:54]([OH:57])(=[O:56])=[O:55])[C:49]2[CH:48]=[CH:47][CH:46]=[C:45]([S:50]([OH:53])(=[O:52])=[O:51])[C:44]=2[CH:43]=[CH:42][CH:41]=1.[C:1]([O:4][CH2:5][C:6]([CH3:20])([CH3:19])[C:7](=[O:18])[CH:8]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 21319211HCID 21319211, compoundHCID 867365311,5-Naphthalenedisulphonic acid octahydrate

Product 1

HCID 23350019HCID 23350019, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A solution of 36.3 g (0.2 mol) of crude 4-acetoxy-1-bromo-1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one in 50 ml of acetone was added dropwise, at the boil, to a suspension of 21 g (0.3 mol) of 1,2,4-triazole and 30g (0.2 mol) of potassium carbonate in 200 ml of acetone. After heating for 15 hours under reflux, the mixture was filtered and the filtrate was concentrated by distilling off the solvent in vacuo. The residue was taken up in 200 ml of methylene chloride and the solution was washed three times with 50 ml of water at a time, dried over sodium sulphate and concentrated. The residue was dissolved in 100 ml of acetone and 36 g (0.1 mol) of 1,5-naphthalenedisulphonic acid octahydrate in 100 ml of acetone were added. The crystalline precipitate which resulted was filtered off and dried. 45 g (45% of theory) of 4-acetoxy-1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one 1,5-naphthalenedisulphonate of melting point 155°-160° C. were obtained.

Workup

  1. temperatureAfter heating for 15 hours
  2. temperatureunder reflux
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. distillationby distilling off the solvent in vacuo
  6. washthe solution was washed three times with 50 ml of water at a time
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in 100 ml of acetone
  10. customThe crystalline precipitate which resulted
  11. filtrationwas filtered off
  12. customdried

Sources & evidence

ORD record
ord-2de565b740bc4da19c8048d8ebc84e84
Source dataset
uspto-grants-1979_05
Patent number
US04154842

Reaction notes

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