Ammonia → 2-Thiophenesulfonamide

HRID 1258368Notes

Reaction equation

HRID 1258368 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[NH3:10].Cl>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH2:10])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 855182-Thiophenesulfonyl chloride

Product 1

HCID 728812-ThiophenesulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

365.3 mg thiophene-2-sulfonyl chloride was dissolved in 5 ml THF, to which at 0° C. was added 1.7 ml NH3 solution drop wise. The resulting mixture was stirred at r.t. for 2 hrs and acidified with conc. HCl at 0° C. to pH=˜2. The organic solvent was removed via rotavap and the aqueous suspension was extracted with ethyl acetate. The extract was combined and washed with saturated NaHCO3 solution, water and brine. Dried over Na2SO4, the organic phase was filtered and the filtrate was concentrated affording the title compound 212 mg (65%) as a white solid, m.p.: 137-139° C.

Workup

  1. customThe organic solvent was removed via rotavap
  2. extractionthe aqueous suspension was extracted with ethyl acetate
  3. washwashed with saturated NaHCO3 solution, water and brine
  4. dry with materialDried over Na2SO4
  5. filtrationthe organic phase was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-94b59f8763cc44ffaa642750bcf4d668
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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