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

HRID 220684Notes

Reaction equation

HRID 220684 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([CH2:13][CH2:14][O:15][CH3:16])[C:9](=[O:12])[NH:10][N:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(#N)C>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]([CH2:13][CH2:14][O:15][CH3:16])[C:9](=[O:12])[N:10]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetate2×HCID 11430Potassium CarbonateHCID 595368995-(5-Chloro-2-thienyl)-4-(2-methoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 59536780Ethyl [3-(5-chloro-2-thienyl)-4-(2-methoxyethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Of the compound from Example 168A, 2.4 g (9.24 mmol) were suspended with 2.55 g (18.48 mmol) of potassium carbonate in 48 ml of acetonitrile. Then 1.08 ml (10.17 mmol) of ethyl chloroacetate were added and the mixture was heated under reflux at 80° C. for 4.5 h. A further 113 mg (0.92 mmol) of ethyl chloroacetate were added, with stirring at 80° C. for 2 h. The suspension was filtered through a layer of silica gel, which was washed with ethyl acetate, and the filtrate was concentrated on a rotary evaporator and dried in an HV. This gave 3.24 g (100% of theory) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. filtrationThe suspension was filtered through a layer of silica gel, which
  3. washwas washed with ethyl acetate
  4. concentrationthe filtrate was concentrated on a rotary evaporator
  5. customdried in an HV

Sources & evidence

ORD record
ord-97f14804966c41879b7f11c195098c59
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

Loading…