ChemicalBook CAS DataBase List Cyclopropanesulfonamide

Cyclopropanesulfonamide synthesis

5synthesis methods

Product Name:Cyclopropanesulfonamide
CAS Number:154350-29-5
Molecular formula:C3H7NO2S
Molecular Weight:121.16

139631-62-2

154350-29-5

Cyclopropanesulfonamide was synthesized as follows: Standard method D (0054) was used, with cyclopropanesulfonyl chloride as the starting material. The procedure was as follows: cyclopropanesulfonyl chloride (0.400 mL, 3.95 mmol) was dissolved in methanol (3.0 mL) and ammonium hydroxide solution (15 mL) at 0 °C or room temperature and the reaction mixture was stirred. After the reaction lasted for 16 hours, methanol was removed by distillation under reduced pressure. Subsequently, the reaction mixture was extracted with ethyl acetate. After combining the organic layers, the reaction was dried using anhydrous magnesium sulfate (MgSO4), filtered and concentrated to give the target product cyclopropanesulfonamide directly without further purification. The final cyclopropanesulfonamide was obtained as a white solid (0.249 g, 52% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6, 300 MHz), and the characteristic peaks were: δ 6.78 (br s, 2H), 2.50-2.46 (m, 1H), 0.89-0.86 (m, 4H).

1189-71-5
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139631-62-2 Synthesis

139631-62-2
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765-30-0
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154350-29-5
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$6.00/1g

Yield:154350-29-5 750 mg (6.19 mmol, 87%)

Reaction Conditions:

with ammonia;triethylamine;trifluoroacetic acid in dichloromethane;tert-butyl alcohol;

Steps:

V Preparation of Sulfonyl Compounds

Preparation of Sulfonyl Compounds Compounds S1, S2, S3, and S4, shown above, were prepared according to procedures described in WO 2005/095403 and PCT/US2005/010494, hereby incorporated by references by their entireties. Specifically, to a solution of chlorosulfonylisocyanate (10 mL, 115 mmol) in CH₂Cl₂ (200 mL) at 0° C. was added t-BuOH (11 mL, 1 eq.). The mixture was stirred for 60 minutes, then added via cannula into a solution of cyclopropylamine (6.6 g) in CH₂Cl₂ (200 mL) with triethylamine (30 mL) at 0° C. concurrently with a solution of triethylamine (50 mL) in CH₂Cl₂ (100 mL) via addition funnel. Internal temperature was maintained below 8° C. Stirred at room temperature after completion of addition for 4 hrs. The reaction was then diluted with CH₂Cl₂ and transferred to a separatory funnel, washed with 1 N HCl (twice, 400 mL each), brine (300 mL), dried (MgSO₄), filtered and concentrated. The product was recrystallized from ethyl acetate/hexanes to yield 16.8 g (71.3 mmol, 62%) of S3. Compound S3 was deprotected with trifluoroacetic acid in CH₂Cl₂ to give compound S4 in quantitative yield. Ammonia gas was bubbled through a gas dispersion tube into THF (40 mL) cooled to 0° C. for 5 minutes. To this solution at 0° C. was added cyclopropylsulfonylchloride (1 gram, 7.1 mmol). The reaction was stirred at room temperature overnight, then filtered through a plug of silica gel, followed by elution with EtOAc to yield 750 mg (6.19 mmol, 87%) of cyclopropylsulfonamide. ¹H-NMR (500 MHz, Methanol-d₄): 4.79 (s, 2H), 2.59-2.54 (m, 1H), 1.06-0.96 (m, 4H).