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

HRID 660856Notes

Reaction equation

HRID 660856 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][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:16](=[O:19])[NH:17][N:18]=2)=[CH:10][CH:9]=1.Cl[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(#N)C>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][N:17]1[C:16](=[O:19])[N:15]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:14]([C:11]2[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=2)=[N:18]1)[CH3:35]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580122805-(4-chlorophenyl)-4-(4-methoxybenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 58012215Ethyl[3-(4-chlorophenyl)-4-(4-methoxyphenylmethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.54 g (18.4 mmol) of potassium carbonate are added to 2.90 g (9.18 mmol) of 5-(4-chlorophenyl)-4-(4-methoxyphenylmethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one from Example 55A and 1.13 g (9.18 mmol) of ethyl chloroacetate in 60 ml acetonitrile and the mixture is heated under reflux overnight with stirring. It is then concentrated, the residue is partitioned between ethyl acetate and water and the aqueous phase extracted three times more with ethyl acetate. By evaporation of the organic phases, combined and dried over magnesium sulphate, 3.58 g (97% of theory) of the target compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. concentrationIt is then concentrated
  4. customthe residue is partitioned between ethyl acetate and water
  5. extractionthe aqueous phase extracted three times more with ethyl acetate
  6. customBy evaporation of the organic phases
  7. dry with materialdried over magnesium sulphate, 3.58 g (97% of theory) of the target compound
  8. customare obtained

Sources & evidence

ORD record
ord-735cfc622841487a849a9216231a326b
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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