4-Nitrobenzenesulfonyl chloride → HCID 19085873, compound

HRID 962739Notes

Reaction equation

HRID 962739 reaction equation
[O:1]=[S:2]1(=[O:17])[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][OH:16].C(N(CC)CC)C.[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([O-:27])=[O:26]>O1CCCC1>[O:17]=[S:2]1(=[O:1])[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][O:16][S:34]([C:31]1[CH:30]=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:33][CH:32]=1)(=[O:35])=[O:36]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 19085906HCID 19085906, compound

Product 1

HCID 19085873HCID 19085873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.73 g of 1,1-dioxido-2-(4-hydroxybutyl)-isothiazolo[5,4-b]pyridin-3(2H)-one and 0.8 mL of triethylamine in 50 mL of dry tetrahydrofuran at 0° C. was added 0.63 g of technical grade 4-nitrobenzenesulfonyl chloride. After 4 h, the solution was filtered and concentrated to dryness under reduced pressure. The residue was dissolved in 100 mL of ethyl acetate, washed with 10 mL of saturated sodium carbonate and dried over MgSO4. Concentration under reduced pressure gave 1.4 g of crude 1,1-dioxido-2-(4-(4-nitrobenzenesulfonyloxy)butyl)-isothiazolo[5,4-b]pyridin-3(2H)-one as an oil. The crude product was a mixture of 4-nitrobenzenesulfonate contaminated with a small amount of chloride by NMR, and was used in the next step without further purification.

Workup

  1. filtrationthe solution was filtered
  2. concentrationconcentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 100 mL of ethyl acetate
  4. washwashed with 10 mL of saturated sodium carbonate
  5. dry with materialdried over MgSO4
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-ba08022c85cf406393424e4a09b039ae
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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