2-Chloro-N,N-dimethyl-5-nitrobenzene-1-sulfonamide → 5-amino-2-chloro-N,N-dimethylbenzene-1-sulfonamide

HRID 1681098Notes

Reaction equation

HRID 1681098 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[Cl:15])(=[O:5])=[O:4]>Cl>[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=1[Cl:15])(=[O:5])=[O:4]

Participants

3

Reactant 1

HCID 201055802-Chloro-N,N-dimethyl-5-nitrobenzene-1-sulfonamide

Product 1

HCID 36139385-amino-2-chloro-N,N-dimethylbenzene-1-sulfonamideYield 49.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 200 g of stannous chloride dihydrate and 250 ml of concentrated hydrochloric acid was cooled to 10° C. To the stirred mixture was added 50 g of N,N-dimethyl-2-chloro-5-nitrobenzenesulfonamide (Example A-2 above) in portions maintaining the temperature of 10° C. After removing the cooling bath, the reaction temperature rose to 55° C. and was held for two hours. The reaction mixture was cooled and filtered to remove the complex of the product with stannic chloride. The product was treated with water to decompose the complex and extracted with methylene chloride. Removal of solvent from the dried extract on a rotary evaporator gave 22 g of the title compound as a solid with a melting point of 125°-126° C.

Workup

  1. temperaturemaintaining the temperature of 10° C
  2. customAfter removing the cooling bath
  3. customrose to 55° C.
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. customto remove the complex of the product with stannic chloride
  7. additionThe product was treated with water
  8. extractionextracted with methylene chloride
  9. customRemoval of solvent from the dried
  10. extractionextract on a rotary evaporator

Sources & evidence

ORD record
ord-e46355b69d0c42ffa29dd06120febacc
Source dataset
uspto-grants-1992_12
Patent number
US05169430

Reaction notes

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