Ammonia → 2,5-Dichlorobenzenesulfonamide

HRID 479268Notes

Reaction equation

HRID 479268 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[S:10](Cl)(=[O:12])=[O:11].Cl>C(#N)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[S:10]([NH2:1])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 794012,5-Dichlorobenzenesulfonyl chloride

Product 1

HCID 2380452,5-Dichlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

170 ml of aqueous solution of 25% ammonia and 500 ml of acetonitrile were ice-cooled and stirred while maintaining the internal temperature at 5° C. or lower. 126 g (0.513 mol) of commercially available 2,5-dichlorobenzenesulfonyl chloride was added dividedly in five times over 1 hour. After completion of the addition, additional 30 minutes' reaction was performed, and then the reaction mixture was poured in a mixed solution of 100 ml of concentrated hydrochloric acid and 1,000 ml of ice water under stirring. The precipitated crystal was collected by filtration, and washed with water. By drying, 100 g of 2,5-dichlorobenzenesulfonamide was obtained as a white crystal (yield 88%).

Workup

  1. temperaturecooled
  2. additionAfter completion of the addition, additional 30 minutes'
  3. customreaction
  4. stirringunder stirring
  5. filtrationThe precipitated crystal was collected by filtration
  6. washwashed with water
  7. customBy drying

Sources & evidence

ORD record
ord-187357487b834a87bcaab5baeb5c809d
Source dataset
uspto-grants-2003_11
Patent number
US06645711B2

Reaction notes

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