Ethanol → N-[2-(4-aminophenylamino)ethyl]-N-methylmethanesulfonamide sulfate

HRID 1393837Notes

Reaction equation

HRID 1393837 reaction equation
[Cl-].[NH4+].[OH2:3].[CH3:4][N:5]([CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[S:6]([CH3:9])(=[O:8])=[O:7].C([OH:24])C>[Zn]>[S:6]([OH:8])([OH:24])(=[O:7])=[O:3].[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][CH2:11][CH2:10][N:5]([CH3:4])[S:6]([CH3:9])(=[O:8])=[O:7])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 23104462N-methyl-N-[2-(4-nitrophenylamino)ethyl]methanesulfonamide

Product 1

HCID 69204989N-[2-(4-aminophenylamino)ethyl]-N-methylmethanesulfonamide sulfate

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of zinc powder (25 g), ammonium chloride (1.1 g), water (11.2 mL), and 96% ethanol (67.5 mL) was brought to reflux in a boiling water bath. N-methyl-N-[2-(4-nitrophenylamino)ethyl]methanesulfonamide (23) (12.3 g, 0.045 mol) was added in portions and heating was continued until the reaction medium decolorized. The resulting mixture was filtered while boiling and the filtrate was recovered onto 3.8 mL of 96% sulfuric acid. The zinc was washed with ethanol, the filtrate was cooled in ice, and the precipitate that formed was filtered off by suction. After recrystallization from 30 mL of ethanol and 30 mL of water, 14.4 g of product were isolated. A second recrystallization from 45 mL of 50% ethanol gave 11.5 g of expected product having the following elemental analyses:

Workup

  1. temperatureto reflux in a boiling water bath
  2. temperatureheating
  3. filtrationThe resulting mixture was filtered
  4. customthe filtrate was recovered onto 3.8 mL of 96% sulfuric acid
  5. washThe zinc was washed with ethanol
  6. temperaturethe filtrate was cooled in ice
  7. customthe precipitate that formed
  8. filtrationwas filtered off by suction
  9. customAfter recrystallization from 30 mL of ethanol and 30 mL of water

Sources & evidence

ORD record
ord-195f2bf1945a41fe8795142af42ca395
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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