Water → 1-{4-[(ethylamino)carbonyl]phenyl}-5-isopropyl-1H-1,2,3-triazole-4-carboxylic acid
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].[C:15]([CH2:20][C:21]([O:23]CC)=[O:22])(=O)[CH:16]([CH3:18])[CH3:17].[O-]CC.[Na+].O>C(O)C>[CH2:11]([NH:10][C:8]([C:7]1[CH:6]=[CH:5][C:4]([N:1]2[C:15]([CH:16]([CH3:18])[CH3:17])=[C:20]([C:21]([OH:23])=[O:22])[N:3]=[N:2]2)=[CH:14][CH:13]=1)=[O:9])[CH3:12]Participants
Conditions
- Temperature
- 50 °C
Procedure
4-Azido-N-ethylbenzamide (0.94 g, 4.70 mmol) and ethyl isobutyrylacetate (1.03 g, 6.10 mmol, 1.3 eq.) were dissolved in ethanol (20 ml), sodium ethoxide (461 mg, 6.10 mmol, 1.3 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 50° C. for 63 hr. Water (20 ml) was added to the reaction mixture, and ethanol was evaporated. The residue was diluted with 2% aqueous sodium carbonate solution (20 ml), and the mixture was washed with ethyl acetate-hexane (2:1, 50 ml). The aqueous layer was acidified (pH<3) with 6N hydrochloric acid and stood still at 0° C. The precipitate was collected by filtration, washed with ice-cold water and dried to give the title compound as a pale-brown powder (1.33 g, 4.39 mmol, 93.4%).
Workup
- customwas evaporated
- additionThe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
- washthe mixture was washed with ethyl acetate-hexane (2:1, 50 ml)
- customstood still at 0° C
- filtrationThe precipitate was collected by filtration
- washwashed with ice-cold water
- customdried
Sources & evidence
- ORD record
- ord-9e65e35c16334611816f50300b27863f
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803822B2
Reaction notes
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