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 574145Notes

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>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][N:10]1[C:9](=[O:12])[N:8]([CH2:13][CH2:14][O:15][CH3:16])[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:11]1)[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

2.4 g (9.24 mmol) of the compound of Example 13A and 2.55 g (18.48 mmol) of potassium carbonate were suspended in 48 ml of acetonitrile. 1.08 ml (10.17 mmol) of ethyl chloroacetate were then added, and the mixture was heated under reflux at 80° C. for 4.5 h. Another 113 mg (0.92 mmol) of ethyl chloroacetate were added, and the mixture was stirred at 80° C. for 2 h. The suspension was filtered through a layer of silica gel, the silica gel was washed with ethyl acetate and the filtrate was evaporated on a rotary evaporator and dried under HV. This gave 3.24 g (100% of theory) of the title compound.

Workup

temperaturethe mixture was heated
filtrationThe suspension was filtered through a layer of silica gel
washthe silica gel was washed with ethyl acetate
customthe filtrate was evaporated on a rotary evaporator
customdried under HV

Sources & evidence

ORD record: ord-a3c37fc3e0b84c4e8108eca3c569a3a7
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034855B2

Reaction notes

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