Hydrochloric Acid → 2-Acetyl-6-chloro-3-nitrobenzenesulfonamide

HRID 2301491Notes

Reaction equation

HRID 2301491 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].[C:16]([O-])(=[O:18])[CH3:17].[K+].C1OCCOCCOCCOCCOCCOC1.Cl>CS(C)=O>[C:16]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 111732852,6-Dichloro-3-nitrobenzene-1-sulfonamide

Product 1

HCID 183734452-Acetyl-6-chloro-3-nitrobenzenesulfonamideYield 79.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2,6-dichloro-3-nitrobenzenesulfonamide (2.04 g, 7.5 mmol), potassium acetate (2.21 g, 22.5 mmol) and 18-crown-6 (5.95 g, 22.5 mmol) in 50 mL of dimethyl sulfoxide was heated to 45° C., for 7 days. The mixture was acidified with 1N aq. HCl, and extracted with ethyl acetate. The organic layer was concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v) gave the desired product (1.67 g, 76%). EI-MS (m/z) 293.1, 295.1 (M−).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customto give the crude material
  4. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane/acetic acid (50/49/1, v/v/v)

Sources & evidence

ORD record
ord-fc4e504cf23c4ab899a31e57d7238369
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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