5-Chloro-4-nitrothiophene-2-sulfonyl chloride → HCID 86632423, compound

HRID 1662922Notes

Reaction equation

HRID 1662922 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(=O)([O-])[O-:15].[Ag+2:18].CCCCCC.C(OCC)(=O)C>C(#N)C.O>[Cl:1][C:2]1[S:6][C:5]([S:7]([O-:15])(=[O:9])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Ag+:18]

Participants

6

Reactant 3

HCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178418647HCID 178418647, compound

Product 1

HCID 86632423HCID 86632423, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-chloro-4-nitrothiophene-2-sulfonyl chloride (0.393 g, 1.5 mmol) in 15 mL of acetonitrile and 2 mL of water was added silver carbonate (0.414 g, 1.5 mmol) in portions in darkness. The resulting suspension was stirred overnight for 3 days, until no starting material is shown on the thin layer chromatography with an eluant of hexane/ethyl acetate (1:4). The mixture was filtered through half an inch of Celite® and the solid was washed with 3×15 mL acetonitrile. The organic filtrate was combined and organic solvent was removed via rotary evaporator to dryness and thus afforded 0.507 g of viscous solid with a yield of 96.4%. The resulting compound was not purified for further reactions. 1HNMR, d6-DMSO: 7.49 (d, 1H, 0.8 Hz)

Workup

  1. filtrationThe mixture was filtered through half an inch of Celite®
  2. washthe solid was washed with 3×15 mL acetonitrile
  3. customorganic solvent was removed via rotary evaporator to dryness and thus afforded 0.507 g of viscous solid with a yield of 96.4%
  4. customThe resulting compound was not purified for further reactions

Sources & evidence

ORD record
ord-18ec2c612b6a4cc3af42b18173f42eb2
Source dataset
uspto-grants-2011_10
Patent number
US08034533B2

Reaction notes

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