Hydrochloric Acid → N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide

HRID 2283344Notes

Reaction equation

HRID 2283344 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH2:14])(=[O:7])=[O:6])[CH:2]=[CH2:3].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:24][C:25]1[CH:26]=[C:27]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1.Cl>O1CCCC1>[CH2:15]([N:4]([CH2:1][CH:2]=[CH2:3])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([Br:24])[CH:26]=1)(=[O:33])=[O:32])(=[O:7])=[O:6])[CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 17943m-Bromobenzenesulphonyl chlorideHCID 57750998N,N-diallyl-4-aminopyridine-3-sulfonamide

Product 1

HCID 57750923N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N,N-diallyl-4-aminopyridine-3-sulfonamide (0.25 g, 1.0 mmol) and cesium carbonate (0.82 g, 2.5 mmol) in tetrahydrofuran (10 mL) was stirred for 5 min, 3-bromobenzenesulfonyl chloride (0.17 mL, 1.2 mmol) was added and the reaction was stirred at room temperature over night. Diluted hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (95:5) as the eluent, gave the title compound in 72% yield.

Workup

  1. stirringthe reaction was stirred at room temperature over night
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-8ae2624dfd3d4edeb08840337274edaf
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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