Sodium Hydroxide → N-(2-Aminophenyl)-N-methylmethanesulfonamide

HRID 1249115Notes

Reaction equation

HRID 1249115 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)[S:3]([CH3:6])(=[O:5])=[O:4].O.O.Cl[Sn]Cl.[OH-].[Na+]>Cl>[NH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 13314625N-Methyl-N-(2-nitrophenyl)methanesulfonamide

Product 1

HCID 13314626N-(2-Aminophenyl)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

50.2 g of N-methyl-N-(2-nitrophenyl)methanesulfonamide, prepared by the procedure of Example 5, is added to 220 ml of concentrated HCl and contacted with 183.3 g of SnCl2.2H2O. The mixture is heated on a steam bath for one hour. The reaction mixture is treated with enough 5-10% NaOH to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C. The crude reaction mixture is then extracted with CH2Cl2. The CH2Cl2 extracts are dried with MgSO4 and then filtered and concentrated on a rotary evaporator. The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step.

Workup

  1. temperatureThe mixture is heated on a steam bath for one hour
  2. temperatureto raise the pH to 9
  3. temperaturewhile maintaining the temperature of the mixture less than 25° C
  4. customThe crude reaction mixture
  5. extractionis then extracted with CH2Cl2
  6. dry with materialThe CH2Cl2 extracts are dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. customThe solid product obtained (38.1 g), m.p. 138°-139°
  10. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-bb7dc1559c364909909eeeee53345a60
Source dataset
uspto-grants-1986_12
Patent number
US04629496

Reaction notes

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