Methyl chloroacetate → Methyl [3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

HRID 660895Notes

Reaction equation

HRID 660895 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH2:20][CH:21]=[CH2:22])[C:16](=[O:19])[NH:17][N:18]=2)=[CH:10][CH:9]=1.Cl[CH2:24][C:25]([O:27][CH3:28])=[O:26]>C(#N)C>[CH3:28][O:27][C:25](=[O:26])[CH2:24][N:17]1[C:16](=[O:19])[N:15]([CH2:20][CH:21]=[CH2:22])[C:14]([C:11]2[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=2)=[N:18]1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 497656025-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 58012233Methyl [3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.87 g (100.35 mmol) of potassium carbonate are added to 21.50 g (91.2 mmol) of 5-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-one from Example 210A and 11.88 g (109.5 mmol) of methyl chloroacetate in 350 ml acetonitrile and the mixture is heated under reflux for 5 hrs with stirring. It is then concentrated and the residue taken up in ethyl acetate is washed with 1 N hydrochloric acid and then with saturated sodium chloride solution. The organic phase is dried over sodium sulphate. After filtration, the filtrate is concentrated in vacuo. After purification by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) 24.00 g (85% of theory) of the target compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 hrs
  3. concentrationIt is then concentrated
  4. washis washed with 1 N hydrochloric acid
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated in vacuo
  8. customAfter purification by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) 24.00 g (85% of theory) of the target compound
  9. customare obtained

Sources & evidence

ORD record
ord-450d319eda3f4da6ba7e306ad09f0398
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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