Cysteamine Hydrochloride → N-methyl-N-hydroxyethyl Acrylamide N,N-dimethyl Acrylamide

HRID 1582374

Reaction equation

HRID 1582374 reaction equation
Cl.NCCS.Cl.Cl.N(C(C1NCCN=1)(C)C)=NC(C1NCCN=1)(C)C.[CH3:26][N:27]([CH3:32])[C:28](=[O:31])[CH:29]=[CH2:30].[CH3:33][N:34]([CH2:39][CH2:40][OH:41])[C:35](=[O:38])[CH:36]=[CH2:37]>O>[CH3:33][N:34]([CH2:39][CH2:40][OH:41])[C:35](=[O:38])[CH:36]=[CH2:37].[CH3:26][N:27]([CH3:32])[C:28](=[O:31])[CH:29]=[CH2:30]

Participants

6

Reactant 4

HCID 9082Cysteamine HydrochlorideHCID 17587N,N-DimethylacrylamideHCID 99491012,2'-Azobis[2-(2-imidazolin-2-yl)propane] dihydrochlorideHCID 10129965N-(2-hydroxyethyl)-N-methylprop-2-enamide

Product 1

HCID 86586140N-methyl-N-hydroxyethyl Acrylamide N,N-dimethyl Acrylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1000 mL three-necked round bottom flask is charged with a solution of 27.26 g (240 mmol) cysteamine hydrochloride in 400 mL deionized water. 390 mg (1.2 mmol) 2,2′-azobis-[2-(2-imidazolin-2-yl) propane] dihydrochloride, 42,35 g (427 mmol) freshly distilled N,N-dimethyl acrylamide, and 38,74 g (300 mmol) distilled N-methyl-N-hydroxyethyl acrylamide are added. An intensive cooler and an internal thermometer are connected to the flask. The apparatus is evacuated to 100 mbar and filled with argon. This is repeated five times. The mixture is heated overnight to 40° C. and then cooled to room temperature. An analytical sample was freeze-dried and the monomer conversion was determined by 1H-NMR spectroscopy. No resonances corresponding to C═C double bonds could be detected, indicating >98% conversion of the monomer.

Workup

  1. additionare added
  2. customThe apparatus is evacuated to 100 mbar
  3. additionfilled with argon
  4. temperatureThe mixture is heated overnight to 40° C.
  5. customAn analytical sample was freeze-dried

Sources & evidence

ORD record
ord-882e26273cd24de587810928ba4cde79
Source dataset
uspto-grants-2004_05
Patent number
US06734281B2

Linked notes

Loading…