Ethanol → 1-(3-aminophenyl)-N,N-dimethylmethanesulfonamide

HRID 1891015Notes

Reaction equation

HRID 1891015 reaction equation
C(O)C.[CH3:4][N:5]([CH3:19])[S:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)(=[O:8])=[O:7].C(=O)([O-])[O-].[Na+].[Na+]>Cl.[Fe].O>[NH2:16][C:12]1[CH:11]=[C:10]([CH2:9][S:6]([N:5]([CH3:19])[CH3:4])(=[O:8])=[O:7])[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 28632733N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamide

Product 1

HCID 432562151-(3-aminophenyl)-N,N-dimethylmethanesulfonamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of iron powder (0.5 g), ethanol (20 ml), water (1 ml) and concentrated hydrochloric acid (5 drops) at reflux was added N,N-Dimethyl-C-(3-nitro-phenyl)-methanesulfonamide (0.5 g). The mixture was then heated under reflux for a further 2 hours then basified with excess sodium carbonate solution, cooled to 60° C., then filtered. The filter cake washed with ethanol and the filtrate evaporated. The crude product was partitioned between ethyl acetate and water, separation and evaporation of the organic phase gave C-(3-Amino-phenyl)-N,N-dimethyl-methanesulfonamide, 0.4 g, sufficiently pure to use.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for a further 2 hours
  4. filtrationfiltered
  5. washThe filter cake washed with ethanol
  6. customthe filtrate evaporated
  7. customThe crude product was partitioned between ethyl acetate and water, separation and evaporation of the organic phase

Sources & evidence

ORD record
ord-6d35f2d12fa04d2283f443769a77ea70
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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