Hydrochloric Acid → N-(2-AMINOETHYL)METHANESULFONAMIDE

HRID 1936768Notes

Reaction equation

HRID 1936768 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][CH2:7][NH:8]C(=O)C)(=[O:4])=[O:3].[ClH:12]>O>[ClH:12].[CH3:1][S:2]([NH:5][CH2:6][CH2:7][NH2:8])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22609770HCID 22609770, compound

Product 1

HCID 22609809N-(2-AMINOETHYL)METHANESULFONAMIDE

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[2-(Methylsulphonamido)ethyl]acetamide (14.5 g, 88.3 mmol) and concentrated hydrochloric acid (100 ml) were dissolved in water (100 ml) and heated to reflux for a total of 3 hours. After cooling, the water was removed in vacuo, and the residue was left for several days at room temperature until crystallisation was underway. Trituration with a mixture of ethanol and ether gave the title compound as a white solid which was dried in vacuo at 60° C. (7.5 g, 42.9 mmol, 49%); δH [2H6]DMSO 8.22 (2H,br s), 7.42 (1H,t), 3.23 (2H,q), 2.87 (3H,s), 2.85-2.95 (2H,m).

Workup

  1. temperatureheated
  2. temperatureto reflux for a total of 3 hours
  3. temperatureAfter cooling
  4. customthe water was removed in vacuo
  5. waitthe residue was left for several days at room temperature until crystallisation
  6. additionTrituration with a mixture of ethanol and ether

Sources & evidence

ORD record
ord-efa6465e5c2c4e9486e20a8da562145c
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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