1H-1,2,4-Triazole → HCID 13269108, compound

HRID 569198Notes

Reaction equation

HRID 569198 reaction equation
Cl[CH2:2][C:3](=[O:17])[C:4]([CH3:16])([CH3:15])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[NH:24]1[CH:28]=[N:27][CH:26]=[N:25]1>CC(C)=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][C:4]([CH3:16])([CH3:15])[C:3](=[O:17])[CH2:2][N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 133228741-Chloro-5-(4-chlorophenoxy)-3,3-dimethylpentan-2-one

Product 1

HCID 13269108HCID 13269108, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 55 g (0.2 mol) of 1-chloro-5-(4-chlorophenoxy)-3,3-dimethyl-2-pentanone in 50 ml of acetone is added dropwise to a mixture of 27.6 g (0.2 mol) of potassium carbonate and 27.6 g (0.4 mol) of 1,2,4-triazole in 400 ml of boiling acetone. The mixture is boiled for a further 3 hours, cooled down to 20° C., filtered and the filtrate is evaporated in vacuo. The oily residue is taken up in 250 ml of ethyl acetate and washed three times with 100 ml of water each time. After drying the organic phase over anhydrous sodium sulphate, it is evaporated in vacupo. the residual crude product (61 g) is dissolved in 250 ml of acetone, and a solution of 57.6 g of naphthalene-1,5-disulphonic acid in 250 ml of acetone is added. The salt which has crystallized out (45.4 g; melting point 188°-190° C.) is suspended in a mixture of 150 ml each of dichloromethane and water and is made alkaline by the addition of 10% strength sodium carbonate solution. The organic phase is separated off, and the aqueous phase is extracted once more with 100 ml of dichloromethane and the combined organic phases are evaporated in vacuo. 30.4 g (49.4% of theory) of 5-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-pentanone are obtained as a pale yellowish liquid of refractive index nD20 =1.5457.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated in vacuo
  3. washwashed three times with 100 ml of water each time
  4. dry with materialAfter drying the organic phase over anhydrous sodium sulphate, it
  5. customis evaporated in vacupo
  6. dissolutionthe residual crude product (61 g) is dissolved in 250 ml of acetone
  7. additiona solution of 57.6 g of naphthalene-1,5-disulphonic acid in 250 ml of acetone is added
  8. customThe salt which has crystallized out (45.4 g; melting point 188°-190° C.)
  9. additionis suspended in a mixture of 150 ml each of dichloromethane and water
  10. additionby the addition of 10% strength sodium carbonate solution
  11. customThe organic phase is separated off
  12. extractionthe aqueous phase is extracted once more with 100 ml of dichloromethane
  13. customthe combined organic phases are evaporated in vacuo

Sources & evidence

ORD record
ord-c143905eae6649e8ade0d5e077ae9ffa
Source dataset
uspto-grants-1988_03
Patent number
US04731452

Reaction notes

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