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

HRID 1462151
Notes
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Reaction equation

HRID 1462151 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 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

  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. custommixtures usually are produced

Sources & evidence

ORD record
ord-b235849190ef41329f95d5e5f5cb938b
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04459229

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes