Cyclohexanesulfonamide

To a solution of 33percent ammonia in water (12 mL), cyclohexenesulfonyl chloride 27(580 µL, 4.00 mmol) was added dropwise over a period of 10 min. at RT whilst the solution was stirred continuously. The solution was then left to stir at RT for a further 90 min. before 1 M aq. HCl was added dropwise until the pH of the solution was 7. The organic product was then extracted into EtOAc (3 x 50 mL).These organic washes were combined and concentrated in vacuo to give sulfonamide 29 as a white solid (592 mg, 91percent). mp 165-167 °C; δTo a solution of cyclohexanesulfonyl chloride (0.1 g, 0.54 mmol) in acetone (1 mL) was added aq NHGeneral procedure: Standard Procedure D for the Preparation of Sulfonamides (0054) A solution of sulfonyl chloride in methanol and ammonium hydroxide solution was stirred at 0° C. or room temperature. After the reaction was complete, methanol was removed under reduced pressure. The solution was extracted with ethyl acetate. The combined organic layers were dried over MgSOA solution of 18.5 mL (37.0 mmol) of 2M cyclohexylmagnesium chloride (TCI Americas) in diethyl ether was added dropwise to a solution of 3.0 mL (37.0 mmol) freshly distilled sulfuryl chloride in 100 mL of hexanes cooled to -78° C. A solution of 18.5 mL (37.0 mmol) of 2M cyclohexylmagnesium chloride (TCI Americas) in ether was added dropwise to a solution of 3.0 mL (37.0 mmol) freshly distilled sulfuryl chloride in 100 mL of hexanes cooled to-78 °C. The mixture was warmed to 0 °C over 1 h and was then carefully concentrated in vacuo. This mixture was redissolved in Et20 (200 mL), washed once with some ice-cold water (200 mL), dried (MgSO4) and concentrated carefullyThis mixture was redissolved in 35 mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stir overnite. The mixture was concentrated in vacuo to a crude yellow solid, the residue filtered through 50g of silica gel using 70percent EtOAc-hexanes as the eluent and was concentrated. The residue was recrystallized from the minimum amount of CHoC12 in hexanes with 1-2 drops of MeOH to afford 1.66 g (30percent) of cyclohexyl- sulfonamide as a white solid : 1H NMR (CDC13) 8 1.11-1. 37 (m, 3H), 1.43-1. 56 (m, 2H), 1.67-1. 76 (m, 1H), 1.86-1. 96 (m, 2H), 2.18-2. 28 (m, 2H), 2.91 (tt, J=12, 3.5 Hz, 1H), 4.70 (bs, 2H) ; 13CH NMR (CDCl3) 8 25.04, 25.04, 26. 56, 62. 74 ; MS m/e 162 (M-1)-.Preparation of cyclohexyl sulfonamide 4. 4c. 4c. EXAMPLE 5 Dicthylethcr (20 mL) is saturated with ammonia then cyclohexancsulfonyl chloride (909 rng; 5 mniol; 1 eq) is added dropwise to the reaction mixture at CFC Ammonia is bubbled through the solution for 10 additional min. The resulting solution is stirred at room temperature overnight. The solvent is evaporated and the residue is trituated in D(

Molecular Weight:163.24
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:163.06669983
Monoisotopic Mass:163.06669983
Topological Polar Surface Area:68.5
Heavy Atom Count:10
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes