Hydrochloric Acid → N-methyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])=[CH:4][C:3]=1[S:17](Cl)(=[O:19])=[O:18].[CH3:21][NH2:22].Cl>O>[CH3:21][NH:22][S:17]([C:3]1[CH:4]=[C:5]([NH:9][S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])(=[O:19])=[O:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonyl chloride (1.5 g), a 40% aqueous solution of methylamine (1 g) and water (20 ml) was stirred at room temperature and allowed to stand overnight at the same temperature. The resultant mixture was made acidic with 5% aqueous hydrochloric acid to precipitate an oily substance, which was then extracted with chloroform. The organic layer was washed with a 5% aqueous solution of hydrochloric acid and water in order and dried over anhydrous magnesium sulfate, followed by concentration. The residue was allowed to stand to give crystals, which were recrystallized from toluene to give 1.1 g of N-methyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide. M.P., 134.5°-135.5° C.
Workup
- customto precipitate an oily substance, which
- extractionwas then extracted with chloroform
- washThe organic layer was washed with a 5% aqueous solution of hydrochloric acid and water in order
- dry with materialdried over anhydrous magnesium sulfate
- concentrationfollowed by concentration
- customto give crystals, which
- customwere recrystallized from toluene
Sources & evidence
- ORD record
- ord-871af1483a884e368cd7fb24b9de1cf0
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04564386
Reaction notes
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