Sulfuric Acid → 4-Amino-3-methyl-N-ethyl-N-(beta-(methanesulfonamido)ethyl)aniline

HRID 436548

Reaction equation

HRID 436548 reaction equation
C1(C)C=CC(S([NH:10][C:11]2[CH:19]=[CH:18][C:14]([NH:15][CH2:16][CH3:17])=[CH:13][C:12]=2[CH3:20])(=O)=O)=CC=1.[CH3:22][S:23]([NH:26][CH2:27][CH2:28]Cl)(=[O:25])=[O:24].C(=O)([O-])O.[Na+].S(=O)(=O)(O)O>C(O)(C)C.CO.O>[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([N:15]([CH2:28][CH2:27][NH:26][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:16][CH3:17])=[CH:13][C:12]=1[CH3:20]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 89092N-(2-Chloroethyl)methanesulphonamideHCID 516892Sodium BicarbonateHCID 214528354-(N-p-Toluenesulfonyl)amino-3-methyl-N-ethylaniline

Product 1

HCID 666934-Amino-3-methyl-N-ethyl-N-(beta-(methanesulfonamido)ethyl)aniline

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 7g of 4-(N-p-toluenesulfonyl)amino-3-methyl-N-ethylaniline, 4g of β-methanesulfonamidoethyl chloride, 2.1g of sodium hydrogen carbonate, 16g of water and 30ml of methanol were refluxed for 5 hours, and then 16g of sulfuric acid were added thereto and the entire reaction system was again refluxed. Next, the reaction solution was condensed to half the original volume and 300ml of isopropyl alcohol were added thereto to separate crystals. The crystals were filtered out and dried to obtain 1.5g of 4-amino-3-methyl-N-(β-methanesulfonamidoethyl)-N-ethylaniline. sesquisulfate. H2O.

Workup

  1. temperaturewere refluxed for 5 hours
  2. temperaturethe entire reaction system was again refluxed
  3. additionwere added
  4. customto separate crystals
  5. filtrationThe crystals were filtered out
  6. customdried

Sources & evidence

ORD record
ord-3e871e83a4f9492bbd2264290214c3df
Source dataset
uspto-grants-1977_02
Patent number
US04009205

Linked notes

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