Hydrochloric Acid → N-[2-(2-(methylamino)ethyl)phenyl]benzenesulfonamide

HRID 366148Notes

Reaction equation

HRID 366148 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])C)(C)(C)C.Cl.C(OCC)(=O)C>ClCCl>[CH3:6][NH:7][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8857Ethyl Acetate2×HCID 20677518N-[2-(2-(phenylsulfonylamino)phenyl)ethyl]-N-methylcarbamic acid tert-butyl ester

Product 1

HCID 10732262N-[2-(2-(methylamino)ethyl)phenyl]benzenesulfonamideYield 128.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2-(2-(Phenylsulfonylamino)phenyl)ethyl]-N-methylcarbamic acid tert-butyl ester (547 mg, 1.4 mmol) was dissolved in dichloromethane (5 ml). 3.1 N hydrogen chloride in ethyl acetate (3 ml, 9.3 mmol) was added. The solution was stirred at room temperature for 1 h. Another portion of 3.1 N hydrogen chloride in ethyl acetate (5 ml, 15.3 mmol) was added. The solution was stirred for another 3.5 h. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silcia (7 g), using dichloromethane/methanol/25% aqueous ammonia 50:10:1 as eluent, to give 521 mg of N-[2-(2-(methylamino)ethyl)phenyl]benzenesulfonamide.

Workup

  1. stirringThe solution was stirred for another 3.5 h
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography on silcia (7 g)

Sources & evidence

ORD record
ord-23d54ef4a9fe4a11b94210cf03f5493f
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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