2-Aminoethanesulfonamide hydrochloride

Add 10 ml of redistilled tetrahydrofuran to a 50 ml three-neck flask at room temperature. Stirring, the system sucks vacuum to replace ammonia, To put it in an atmosphere of 1.0 atmosphere of ammonia, 1.5 g of the compound (2-bromoethylsulfonyl chloride) was dissolved in 10 ml of dry tetrahydrofuran, 10 minutes into the system through constant pressure dropping funnel, It can be observed that a white solid has formed in the system. Continue stirring the reaction for 3h, Solution clarification, White agglomerates form at the bottom. At 30°C, the solvent was evaporated to dryness, and the solution was adjusted to pH between 7 and 8 by adding saturated sodium bicarbonate solution. Methylene chloride was added for extraction several times, dried over anhydrous sodium sulfate, evaporated to dryness, and then beaten with ethyl acetate. Filter to obtain a white solid; Slowly add 7.2ml of 1M ethanol solution in hydrochloric acid. Ensure that the reaction is performed at 20 °C ~ 25 °C, 0.5 hours; Ethanol and water were evaporated to dryness, beaten with acetonitrile at 70° C. to 80° C., and suction-filtered to obtain 1.10 white powdery solid with a yield of 94.3percent.e. Synthesis of 2-sulfonamidoethylamine hydrochloride: 2-formamidoethylsulfonamide was added to anhydrous diethyl ether. The mixture was stirred for 3h under hydrogen chloride gas, , filtrated, the filter cake was washed with anhydrous diethyl ether, and dried to obtain 4.6g of white solid, yield 87percent.2-formamidoethylsulfonamide was added to anhydrous diethyl ether. The mixture was stirred for 3 h under hydrogen chloride gas, filtrated, the filter cake was washed with anhydrous diethyl ether, and dried to obtain 4.6 g of white solid, yield 87percent.General method B: deprotection of phthalimido sulfonamides to their corresponding primary amines. The following procedure is representative for the synthesis of aminoethane- or aminopropane sulfonamides; [Show Image] 2-aminoethanesulfonamide hydrochloride; A suspension of 2-phthalimidoethanesulfonamide (1.52 g, 6.78 mmol) was heated at reflux in EtOH (30 ml) after which hydrazine (0.36 ml, 7.5 mmol) (64percent in water) was added. After 3 hours a precipitate formed that was removed by filtration. The filtrate was evaporated to dryness and added to water (150 ml). The aqueous suspension was acidified with conc. HCI and residual insoluble material was filtered off. The filtrate was evaporated to dryness and the crude sulfonamide was recrystallized from EtOH/water (9:1) to yield the final product as 764 mg (64percent) of a solid. General procedure: To a solution of M-3 (0.80 g, 4.00 mmol) in ethanol (30 mL), hydrazine hydrate (80percent, 0.30 g, 4.80 mmol) was added. After refluxed for 7 h, a white precipitate formed that was removed by filtration. The filtrate was evaporated to dryness and added to water (100 mL). The aqueous suspension was acidified with conc. HCl, and residual insoluble material was filtered off. The clear filtrate was evaporated to give amine-17. Amine-20 was synthesized as the same procedure of amine-17. Yield: 49.3percent; 1H NMR (400 MHz, D2O) δ 3.51 (t, J= 6.3 Hz, 1H), 3.40 (t, J= 6.3 Hz, 1H); 13C NMR (100 MHz, D2O) δ 51.00, 34.28.To the reaction flask was added 108.1 g of compound 5 (0.42 mol), 162 mL of water and 162 mL of concentrated hydrochloric acid (37 wtpercent), and the temperature was raised to reflux for 1 h.After the reaction, the temperature was lowered to 55 ° C, the concentration was reduced to 108 mL, 648 mL of methanol and 1 g of activated carbon were added and the mixture was refluxed for 0.5 h. The filtrate was heated to 5 ± 2 ° C and precipitated for 2 h. Crystalline powder Compound 1, purity 99.3percent (HPLC), yield 91.0percent.

Molecular Weight:160.62
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:160.0073264
Monoisotopic Mass:160.0073264
Topological Polar Surface Area:94.6
Heavy Atom Count:8
Complexity:121
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes