Ammonia → 2,6-Dichlorobenzenesulfonamide

HRID 2301489Notes

Reaction equation

HRID 2301489 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].[NH3:13]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([NH2:13])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 5221832,6-Dichlorobenzenesulfonylchloride

Product 1

HCID 27580592,6-DichlorobenzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2,6-dichlorobenzenesulfonyl chloride (10.50 g, 42.77 mmol) in 100 mL of pyridine was added dropwise to 100 mL of pyridine while anhydrous ammonia gas was bubbled through the solution. After 4 hours at 0° C., the mixture was acidified to pH>1 with 6N aq. HCl, then extracted with ethyl acetate. The combined organic layer was then dried (Na2SO4) and concentrated to give the desired product (8.69 g, 90%). EI-MS (m/z) 225.0, 227.1 (M−).

Workup

  1. customwas bubbled through the solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was then dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74c0995ab0c645c3add4210a467d033a
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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