2-Mercaptoethanol → N-acryloylpyrroline

HRID 916527Notes

Reaction equation

HRID 916527 reaction equation
[C:1]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].SCCO.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N.CCCCCC>C(OCC)(=O)C>[C:1]([N:5]1[CH2:9][CH2:8][CH:7]=[CH:6]1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 8058HexaneHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)HCID 1820551-(Pyrrolidin-1-yl)prop-2-en-1-one

Product 1

HCID 22153749N-acryloylpyrrolineYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7.5 parts of exemplified compound 1-1, compound represented by Formula (I), and 2.5 parts of N-acryloylpyrrolidine were dissolved in 8 parts of ethyl acetate. 0.033 parts of 2-mercaptoethanol was added to the resultant solution. Polymerization was carried out in the presence of 0.02 parts of 2,2′-azobis(2,4-dimethylvaleronitrile) (V-65™ manufactured by Wako Pure Chemical Industries, Ltd.,) serving as a polymerization initiator at a surrounding temperature of 70° C. for 7 hours under nitrogen flow. After the completion of the polymerization, the resultant polymer solution was added to 100 parts of hexane to precipitate a product. As a result, 9.5 parts of exemplified polymer 2-18 was be produced by radical polymerization of the above-mentioned compound 1-1 and N -acryloylpyrroline (yield: 95%).

Workup

  1. customPolymerization
  2. customAfter the completion of the polymerization
  3. customto precipitate a product

Sources & evidence

ORD record
ord-bd826ad48ef8414283b8fc447fc262a1
Source dataset
uspto-grants-2007_09
Patent number
US07270928B2

Reaction notes

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