Sulfuric Acid → 2-{[Ethyl(phenyl)amino]methyl}benzene-1-sulfonic acid

HRID 1583629Notes

Reaction equation

HRID 1583629 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

HCID 1118Sulfuric AcidHCID 7098N-Ethyl-N-benzylanilineHCID 24681Fuming sulfuric acid

Product 1

HCID 201467222-{[Ethyl(phenyl)amino]methyl}benzene-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a 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-Benzylines containing groups such as alkyl, alkoxy, and halogen in the ortho, meta, or para positions of the benzyl group may also 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

  1. additionTo this solution is added, at 50°-60° C.
  2. customprecipitates on standing
  3. filtrationis collected by filtration
  4. washwashed with water
  5. customdried
  6. additionN-Benzylines containing groups such as alkyl, alkoxy, and halogen in the ortho, meta, or para positions of the benzyl group
  7. custommixtures usually are produced

Sources & evidence

ORD record
ord-9f695b40c6c5420b8e416f0b4d27b7a8
Source dataset
uspto-grants-1985_11
Patent number
US04552951

Reaction notes

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