2-Mercaptoethanol → HCID 86730811, compound

HRID 2209315Notes

Reaction equation

HRID 2209315 reaction equation
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:10][N:11]([CH3:16])[C:12](=[O:15])[CH:13]=[CH2:14].[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19].N(C(C1NCCN=1)(C)C)=NC(C1NCCN=1)(C)C.SCCO>CS(C)=O.C(OCC)(=O)C>[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:10][N:11]([CH3:16])[C:12](=[O:15])[CH:13]=[CH2:14].[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19]

Participants

8

Reactant 5

HCID 15672-MercaptoethanolHCID 6581Acrylic AcidHCID 133602-Hydroxyethyl MethacrylateHCID 17587N,N-DimethylacrylamideHCID 887152,2'-Azobis(2-(2-imidazolin-2-yl)propane)

Product 1

HCID 86730811HCID 86730811, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Into a 200 mL three-necked flask, 2-hydroxyethyl methacrylate (3.25 g, 0.025 mol) as the monomer having a hydroxy group, N,N-dimethylacrylamide (4.96 g, 0.050 mol) as the monomer having an amide group, acrylic acid (1.80 g, 0.025 mol) as the acidic monomer, dimethylsulfoxide (41.0 g) as a solvent, a polymerization initiator VA-061 (Wako Pure Chemical Industries, Ltd., 0.016 g, 0.062 mmol), and 2-mercaptoethanol (2-ME, 43 μL, 0.62 mmol) were added, and the three-necked flask was equipped with a three-way cock, a reflux condenser, a thermometer, and a mechanical stirrer. A monomer concentration was 20% by mass. After inside of the three-necked flask was degassed with a vacuum pump and argon replacement was carried out for 3 times, the mixture was stirred at 60° C. for 0.5 hours, and thereafter, the temperature was raised to 70° C. and the mixture was stirred for 4.5 hours. After completion of the polymerization, the polymerization reaction liquid was cooled to room temperature and the liquid was poured to 500 mL of ethyl acetate and the obtained mixture was left to stand for one night. In the next day, a supernatant liquid was removed by decantation. The obtained solid content was washed 10 times with methanol/n-hexane=5 mL/50 mL. The solid content was dried at 60° C. for one night with a vacuum drier. After liquid nitrogen was poured to the solid content and the solid content was fragmentized with a spatula, the solid content was dried at 60° C. for 3 hours with a vacuum drier. Molecular weights of thus obtained copolymer were a Mn of 22 kD and a Mw of 42 kD (Mw/Mn=1.89).

Workup

  1. customthe three-necked flask was equipped with a three-way cock, a reflux condenser
  2. customAfter inside of the three-necked flask was degassed with a vacuum pump and argon replacement
  3. temperaturethe temperature was raised to 70° C.
  4. stirringthe mixture was stirred for 4.5 hours
  5. customAfter completion of the polymerization
  6. customthe polymerization reaction liquid
  7. temperaturewas cooled to room temperature
  8. waitthe obtained mixture was left
  9. waitto stand for one night
  10. customIn the next day, a supernatant liquid was removed by decantation
  11. washThe obtained solid content was washed 10 times with methanol/n-hexane=5 mL/50 mL
  12. customThe solid content was dried at 60° C. for one night with a vacuum drier
  13. additionAfter liquid nitrogen was poured to the solid content
  14. customthe solid content was dried at 60° C. for 3 hours with a vacuum drier

Sources & evidence

ORD record
ord-70ebbb869265442c9908b13d3bf17879
Source dataset
uspto-grants-2016_06
Patent number
US09377562B2

Reaction notes

Loading…