Hydrochloric Acid → 2H-1,2,4-Benzothiadiazine-3-acetic acid, 7-[(methylsulfonyl)amino]-, 1,1-dioxide
Reaction equation
C[O:2][C:3](=[O:23])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:9]=1[S:19](=[O:22])(=[O:21])[NH2:20])=O.[OH-].[Na+].Cl>>[CH3:18][S:15]([NH:14][C:11]1[CH:12]=[CH:13][C:8]2[NH:7][C:5]([CH2:4][C:3]([OH:2])=[O:23])=[N:20][S:19](=[O:22])(=[O:21])[C:9]=2[CH:10]=1)(=[O:17])=[O:16]Participants
Conditions
- Temperature
- 23 °C
Procedure
N-(4-methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid methyl ester (prepared as described in Example 1g, 1.35 kg, 3.69 mol) was added to 3.8 wt. % aqueous sodium hydroxide solution (14.0 kg). The resulting mixture was stirred at 23° C. for 30 h, and was then cooled to 0° C. A 2.0 M aqueous hydrochloric acid solution (9.72 L) was slowly added, stirring at 0° C. was continued for 30 min, and the mixture was then filtered. The solid was washed with water (1.4 L), and was then slurried in a mixture of methanol (1.4 L) and diethyl ether (2.7 L). After filtration, the solid was washed with diethyl ether (2×1.4 L) and was further dried in vacuo at 23° C. to afford the desired product, (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (1.07 kg, 3.21 mol, 87%), as a light brown solid.
Workup
- temperaturewas then cooled to 0° C
- stirringstirring at 0° C.
- waitwas continued for 30 min
- filtrationthe mixture was then filtered
- washThe solid was washed with water (1.4 L)
- additionwas then slurried in a mixture of methanol (1.4 L) and diethyl ether (2.7 L)
- filtrationAfter filtration
- washthe solid was washed with diethyl ether (2×1.4 L)
- customwas further dried in vacuo at 23° C.
Sources & evidence
- ORD record
- ord-3e41cc4b048540aa8b511cdd8cab3b9c
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765741B2
Reaction notes
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