Cyclopropanesulfonamide synthesis

5synthesis methods

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

1189-71-5
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$18.00/5g

139631-62-2 Synthesis

139631-62-2
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765-30-0
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$10.00/25g

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).