2-Aminobenzenesulfonamide → HCID 47337178, compound

HRID 2283310Notes

Reaction equation

HRID 2283310 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[Cl:12][C:13]1[S:17][C:16]([S:18](Cl)(=[O:20])=[O:19])=[CH:15][CH:14]=1>N1C=CC=CC=1>[Cl:12][C:13]1[S:17][C:16]([S:18]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8](=[O:9])(=[O:10])[NH2:11])(=[O:20])=[O:19])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 27339255-Chlorothiophene-2-sulfonyl chloride

Product 1

HCID 47337178HCID 47337178, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-aminobenzenesulfonamide (172 mg) in pyridine (3 ml) was added 5-chlorothiophene-2-sulfonyl chloride (217 mg) and the resulting mixture was heated at 60° C. for 18 h. The mixture was concentrated and then partitioned between DCM (20 ml) and 2N HCl (10 ml). The organics were separated, dried (MgSO4) and evaporated to a gum which was purified by silica chromatography eluting with a gradient of ethyl acetate/hexane to give the title compound as a solid (201 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between DCM (20 ml) and 2N HCl (10 ml)
  3. customThe organics were separated
  4. dry with materialdried (MgSO4)
  5. customevaporated to a gum which
  6. customwas purified by silica chromatography
  7. washeluting with a gradient of ethyl acetate/hexane

Sources & evidence

ORD record
ord-ab085164bf294c1e8ca31eb752f980f8
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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