Ammonia → 2,6-Dichlorobenzenesulfonamide

HRID 432602Notes

Reaction equation

HRID 432602 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].Cl>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

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 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 into 100 mL of pyridine dropwise while anhydrous ammonia gas was passing through the solution simultaneously for 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. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was then dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-83e29e5ccda24022b928c611277eb315
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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