Ammonium Hydroxide → 2,3-Dichlorobenzenesulfonamide

HRID 236517Notes

Reaction equation

HRID 236517 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[OH-].[NH4+:14]>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH2:14])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27342222,3-Dichlorobenzene-1-sulfonyl chloride

Product 1

HCID 83179472,3-Dichlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 60.0 g of 2,3-dichlorobenzenesulfonyl chloride in 500 mL of tetrahydrofuran at 0° C. was added 30 mL of concentrated ammonium hydroxide (30%) dropwise at a rate that maintained the temperature below 15° C. After an additional stirring period of 0.5 hr, the tetrahydrofuran was evaporated under reduced pressure. The resultant solid residue was triturated with 500 mL of water, filtered, and the collected solid washed twice with 100-mL portions of water and dried to yield 52 g of 2,3-dichlorobenzenesulfonamide as a tan solid, m.p. 210°-226° C.; IR (nujol): 3360, 3250, 1370, 1175, 1165 cm-1.

Workup

  1. temperaturemaintained the temperature below 15° C
  2. customthe tetrahydrofuran was evaporated under reduced pressure
  3. customThe resultant solid residue was triturated with 500 mL of water
  4. filtrationfiltered
  5. washthe collected solid washed twice with 100-mL portions of water
  6. customdried

Sources & evidence

ORD record
ord-e038212b29fc4d82b0b4d1d85de1e186
Source dataset
uspto-grants-1987_02
Patent number
US04645527

Reaction notes

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