Hydrochloric Acid → 7-(4-Morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid
Reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]4[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([O:27]C)=[O:26])=[CH:18][C:17]=4[CH:29]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C.C1COCC1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]4[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([OH:27])=[O:26])=[CH:18][C:17]=4[CH:29]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:6]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (550 mg) in ethanol/THF (15 ml/15 ml) was added at room temperature 1N sodium hydroxide solution (1.6 ml), and the mixture was stirred for 18 hours. To the mixture was added 1N hydrochloric acid (1.6 ml), and the mixture was concentrated under reduced pressure. Precipitated crystals were collected by filtration and washed with 2-propanol and diethylether to give yellow crystals of 7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (268.9 mg). The mother liquor was concentrated, and the resulting solid was collected by filtration (177 mg). (Second crystals, Purity: about 50%)
Workup
- concentrationthe mixture was concentrated under reduced pressure
- customPrecipitated crystals
- filtrationwere collected by filtration
- washwashed with 2-propanol and diethylether
Sources & evidence
- ORD record
- ord-71129e07f87f41a8b211d8bb3d0b8121
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235771B1
Reaction notes
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