2,3-Dichlorobenzene-1-sulfonyl chloride → HCID 68779175, compound

HRID 2283308Notes

Reaction equation

HRID 2283308 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[S:22]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:11])=[O:12])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 112526652-Amino-5-methoxybenzenesulfonamide

Product 1

HCID 68779175HCID 68779175, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-methoxy-benzenesulfonamide (2.73 g, 13.43 mmol) in pyridine (25 mL), 2,3-dichlorobenzenesulfonyl chloride (3.68 g, 15.0 mmol) was added slowly at 0° C. The reaction mixture was stirred at RT overnight and then concentrated under reduced pressure. The residue was then partitioned between ethyl acetate and 1N HCl. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash column chromatography using ethyl acetate/hexane (1:1) to afford the title compound (4.8 g, 87%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was then partitioned between ethyl acetate and 1N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-70767c4f367b4dbd8a20d3392b648a09
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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