Ammonia → tetrahydrothiophene-3-sulfonamide 1,1-dioxide

HRID 1914711Notes

Reaction equation

HRID 1914711 reaction equation
[NH3:1].[CH2:2]1[CH:8]([S:9](Cl)(=[O:11])=[O:10])[CH2:7][S:4](=[O:6])(=[O:5])[CH2:3]1>O1CCOCC1.CO>[S:4]1(=[O:6])(=[O:5])[CH2:3][CH2:2][CH:8]([S:9]([NH2:1])(=[O:11])=[O:10])[CH2:7]1

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 2772263tetrahydrothiophene-3-sulfonyl chloride 1,1-dioxide

Product 1

HCID 2729233tetrahydrothiophene-3-sulfonamide 1,1-dioxideYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dioxane (30 mL) is saturated with ammonia and cooled down to 0° C. A solution of tetrahydrothiophene-3-sulfonyl chloride 1,1-dioxide (0.5 g; 2.3 mmol; 1 eq) in dioxane (5 mL) is then added dropwise over 10 min. The reaction mixture is allowed to return to room temperature and stirred for 3 h while keeping ammonia bubbling. The suspension is filtered through a short plug of silica using dioxane as eluent, and the resulting solution is concentrated in vacuo to give a slightly yellow oil. The oil is taken up in MeOH and the solvent is evaporated to dryness to afford 0.37 g (81%) of the title compound as a beige solid. 1H NMR (DMSO-d6) δ 7.25 (s, 2H), 3.98 (quint., J=8.3 Hz, 1H), 3.49 (dd, J=14.0, 9.1 Hz, 1H), 3.38-3.14 (m, 3H), 2.50-2.24 (m, 2H).

Workup

  1. customto return to room temperature
  2. filtrationThe suspension is filtered through a short plug of silica
  3. concentrationthe resulting solution is concentrated in vacuo
  4. customto give a slightly yellow oil
  5. customthe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-f084eda25ef94341ade86a0083013a4f
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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