Ethyl 3-oxohexanoate → 1-[4-[(ethylamino)carbonyl]phenyl]-5-propyl-1H-1,2,3-Triazole-4-carboxylic acid

HRID 1717250Notes

Reaction equation

[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:16]([CH2:23][CH2:24][CH3:25])[CH2:17][C:18]([O:20]CC)=[O:19].[O-]CC.[Na+]>C(O)C>[CH2:11]([NH:10][C:8]([C:7]1[CH:6]=[CH:5][C:4]([N:1]2[C:16]([CH2:23][CH2:24][CH3:25])=[C:17]([C:18]([OH:20])=[O:19])[N:3]=[N:2]2)=[CH:14][CH:13]=1)=[O:9])[CH3:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-azido-N-ethylbenzamide (0.73 g) obtained in Example 43a) and ethyl 3-keto-n-hexanoate (0.77 ml) in ethanol (20 ml) was added 20% sodium ethoxide in ethanol solution (1.85 ml) at room temperature, and the mixture was stirred overnight at 60° C. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with water, and washed with ethyl acetate. The aqueous layer was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a white solid (1.13 g, 98%).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was evaporated under reduced pressure
additionThe residue was diluted with water
washwashed with ethyl acetate
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-c0c645fd5ad24b98ad332e1e722da117
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803822B2

Reaction notes

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