Hydrochloric Acid → N-(2-Aminoethyl)methanesulfonamide dihydrochloride

HRID 2402237Notes

Reaction equation

HRID 2402237 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][CH2:7][NH:8]C(=O)OC(C)(C)C)(=[O:4])=[O:3].[ClH:16].O1CCOCC1.C(OCC)(=O)C>C(OCC)C>[ClH:16].[ClH:16].[NH2:8][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 47454467tert-Butyl {2-[(methanesulfonyl)amino]ethyl}carbamate

Product 1

HCID 86638021N-(2-Aminoethyl)methanesulfonamide dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl {2-[(methylsulfonyl)amino]ethyl}carbamate (21 g, 88 mmol) was stirred in a solution of 4 N hydrogen chloride in 1,4-dioxane (97 mL, 388 mmol) for 30 minutes. Trituration with ethyl acetate and hexanes followed by diethyl ether and hexanes gave the desired compound as a gum (19 g, 100%). LCMS calculated for C3H11N2O2S (M+H)+: m/z=139.0.

Sources & evidence

ORD record
ord-06ead5b5c67c46df89087090a003be80
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

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