Hydrochloric Acid → 2-(2-Propanesulfonylamino-1,3-thiazol-4-yl)glyoxylic acid
Reaction equation
[CH2:1]([S:4]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:19])[C:14]([O:16]CC)=[O:15])[N:12]=1)(=[O:6])=[O:5])[CH2:2][CH3:3].[OH-].[Na+].Cl>>[CH2:1]([S:4]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:19])[C:14]([OH:16])=[O:15])[N:12]=1)(=[O:6])=[O:5])[CH2:2][CH3:3]Participants
Procedure
A mixture of ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-propanesulfonylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate, (12.0 g.) and 1N sodium hydroxide aqueous solution (93 ml.) was stirred for 1 hour under ice-cooling. After the reaction, to the reaction mixture was added 1N hydrochloric acid (93 ml.) and the mixture was extracted with ethyl acetate under saturation with sodium chloride. The extract was washed with a saturated aqueous solution of sodium chloride and dried. The solvent was distilled off from the extract, and the residue was washed in diethyl ether, collected by filtration and dried to give 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)glyoxylic acid, which can be represented as 2-(2-propanesulfonylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylic acid, (7.3 g.), mp. 148° to 150° C.
Workup
- temperaturecooling
- customAfter the reaction
- extractionthe mixture was extracted with ethyl acetate under saturation with sodium chloride
- washThe extract was washed with a saturated aqueous solution of sodium chloride
- customdried
- distillationThe solvent was distilled off from the extract
- washthe residue was washed in diethyl ether
- filtrationcollected by filtration
- customdried
Sources & evidence
- ORD record
- ord-f00213a126c340028e95cc6970cd37f9
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04560765
Reaction notes
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