Sodium Hydroxide → 5-butyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid

HRID 1717283Notes

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]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][C:18]([O:20]C)=[O:19].C[O-].[Na+].[OH-].[Na+]>CO.O>[CH2:22]([C:16]1[N:1]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)[N:2]=[N:3][C:17]=1[C:18]([OH:20])=[O:19])[CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-azido-N-ethylbenzamide (1.00 g) obtained in Example 43a) and methyl 3-oxoheptanoate (1.10 g) in methanol (50 ml) was added a solution of sodium methoxide in methanol (1.35 g, 28%). The reaction mixture was stirred at room temperature for 8 hr and at 70° C. for 3 hr, and 1M aqueous sodium hydroxide solution (11 ml) was added. The reaction mixture was stirred at 70° C. for 1 hr, cooled to room temperature, diluted with water, and methanol was evaporated under reduced pressure. The residual aqueous solution was acidified (pH=1) with 1M hydrochloric acid under ice-cooling, the insoluble material was collected by filtration and washed with water to give the title compound as a brown powder (1.66 g, 99%).

Workup

stirringThe reaction mixture was stirred at 70° C. for 1 hr
temperaturecooled to room temperature
customwas evaporated under reduced pressure
temperaturecooling
filtrationthe insoluble material was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-797dcace14ca41bb99e2cda652792ea3
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803822B2

Reaction notes

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