Sodium Hydroxide → 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

HRID 586949Notes

Reaction equation

[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([C:25]4[CH:30]=[CH:29][C:28]([S:31](=[O:36])(=[O:35])[N:32]([CH3:34])[CH3:33])=[CH:27][CH:26]=4)[CH2:23][CH2:22][C:21]([C:37]([O:39]C)=[O:38])=[CH:20][C:19]=3[CH:41]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([C:25]4[CH:26]=[CH:27][C:28]([S:31](=[O:35])(=[O:36])[N:32]([CH3:33])[CH3:34])=[CH:29][CH:30]=4)[CH2:23][CH2:22][C:21]([C:37]([OH:39])=[O:38])=[CH:20][C:19]=3[CH:41]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

In methanol (50 ml) and THF (50 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.34 g). To the solution was added 1N sodium hydroxide solution (10 ml), and the mixture was stirred at room temperature at 60° C. for 1 hour, concentrated, neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated to give 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.33 g) as yellow crystals.

Workup

concentrationconcentrated
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-3ff31be81d6149b2896132044f8809b7
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

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