Sulfuric Acid → 2-{[Ethyl(phenyl)amino]methyl}benzene-1-sulfonic acid
Reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[CH2:6]([N:13]([CH2:20][CH3:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.OS(O)(=O)=O.O=S(=O)=O>O>[CH2:20]([N:13]([CH2:6][C:7]1[C:8]([S:1]([OH:3])(=[O:5])=[O:2])=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To 30.0 g. of 100% sulfuric acid is added N-benzyl-N-ethylaniline (30.0 g) dropwise below about 50° C. To this solution is added, at 50°-60° C., 60% oleum (30.0 g.) with good stirring. The mixture is stirred and heated at about 60° C. for three hours and then drowned into 200 ml of water. The free sulfonic acid which is mostly the meta isomer with a small amount of para, precipitates on standing and is collected by filtration, washed with water, and dried. N-Benzylanilines containing groups such as alkyl, alkoxy, and halogen in the ortho, meta, or para positions of the benzyl group may be sulfonated by this procedure. The exact location of the sulfonic acid group in these cases is often not known and mixtures usually are produced.
Workup
- additionTo this solution is added, at 50°-60° C.
- customprecipitates on standing
- filtrationis collected by filtration
- washwashed with water
- customdried
- custommixtures usually are produced
Sources & evidence
- ORD record
- ord-b235849190ef41329f95d5e5f5cb938b
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04459229
Reaction notes
Loading…