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

HRID 660854Notes

Reaction equation

HRID 660854 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH:20]3[CH2:22][CH2:21]3)[C:16](=[O:19])[NH:17][N:18]=2)=[CH:10][CH:9]=1.Cl[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(#N)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][N:17]1[C:16](=[O:19])[N:15]([CH:20]2[CH2:22][CH2:21]2)[C:14]([C:11]2[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=2)=[N:18]1)[CH3:29]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 58011757Ethyl [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

586 mg (4.24 mmol) of potassium carbonate are added to 500 mg (2.12 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one from Example 36A and 260 mg (2.12 mmol) of ethyl chloroacetate in 10 ml acetonitrile and the mixture is heated under reflux with stirring for 2 hours. It is then concentrated, the residue taken up in water is extracted with dichloromethane, the organic phase dried over sodium sulphate and again concentrated. After purification by flash chromatography over silica gel (eluent: first dichloromethane, then dichloromethane/methanol 100:1) 448 mg (66% of theory) of the target compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. concentrationIt is then concentrated
  4. extractionis extracted with dichloromethane
  5. dry with materialthe organic phase dried over sodium sulphate
  6. concentrationagain concentrated
  7. customAfter purification by flash chromatography over silica gel (eluent
  8. customfirst dichloromethane, then dichloromethane/methanol 100:1) 448 mg (66% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-2689912a8a144a7287cf86e2ee00e50c
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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