Acrylic Acid → N-propan-2-ylprop-2-enamide;prop-2-enoic acid

HRID 227204

Reaction equation

HRID 227204 reaction equation
C(OS([O-])(=O)=O)CCCCCCCCCCC.[Na+].[CH:19]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])([CH3:21])[CH3:20].[C:27]([OH:31])(=[O:30])[CH:28]=[CH2:29].C(C=CC(N)=O)C=CC(N)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>O>[CH:19]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])([CH3:21])[CH3:20].[C:27]([OH:31])(=[O:30])[CH:28]=[CH2:29]

Participants

7

Reactant 5

HCID 6581Acrylic AcidHCID 16637N-IsopropylacrylamideHCID 24412Potassium PersulfateHCID 3423265Sodium Lauryl SulfateHCID 53800990Methylene-bisacrylamide

Product 1

HCID 157470N-propan-2-ylprop-2-enamide;prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Sodium dodecylsulfate (20 mg), N-isopropylacrylamide (2.7 g), acrylic acid (172 mg), and methylenebisacrylamide (121 mg) are dissolved in 200 ml of water, and, after a 30 minute stirring at 70° C. in a nitrogen atmosphere, a polymerization initiator (potassium persulfate 9.2 mg) is added, followed by 4 hours of stirring. The obtained particles (precursor of Example 2-2) are purified in water by means of dialysis, and then lyophilized. These particles (700 mg) are then dispersed in tetrahydrofuran (30 ml)/dimethylformamide (10 ml), and a tetrahydrofuran (10 ml)/dimethylformamide (50 ml) solution of dicyclohexylcarbodiimide (800 mg), hydroxybenzotriazole (500 mg), and 2,2′-(ethylenedioxy)bis(ethylamine) (1.14 g) is added at room temperature, followed by an overnight stirring. The particles are then dialyzed and lyophilized. They are dispersed in methanol (70 ml), to which 1 g of the chemical compound of Synthetic example 1 is added, followed by a 6 hour stirring at room temperature; this mixture is cooled in an ice bath, 2.8 g of sodium cyanotrihydroborate is added, followed by an overnight stirring at room temperature. The obtained particles are dialyzed in water to obtain the target N-isopropylacrylamide/acrylic acid copolymer particles (620 mg) having phosphorylcholine groups directly on the particle surface.

Workup

  1. waitfollowed by 4 hours
  2. stirringof stirring
  3. customThe obtained particles (precursor of Example 2-2) are purified in water by means of dialysis
  4. additionThese particles (700 mg) are then dispersed in tetrahydrofuran (30 ml)/dimethylformamide (10 ml)
  5. additiona tetrahydrofuran (10 ml)/dimethylformamide (50 ml) solution of dicyclohexylcarbodiimide (800 mg), hydroxybenzotriazole (500 mg), and 2,2′-(ethylenedioxy)bis(ethylamine) (1.14 g) is added at room temperature
  6. waitfollowed by an overnight
  7. stirringstirring
  8. customThe particles are then dialyzed
  9. additionThey are dispersed in methanol (70 ml), to which 1 g of the chemical compound of Synthetic example 1
  10. additionis added
  11. waitfollowed by a 6 hour
  12. stirringstirring at room temperature
  13. temperaturethis mixture is cooled in an ice bath
  14. addition2.8 g of sodium cyanotrihydroborate is added
  15. waitfollowed by an overnight
  16. stirringstirring at room temperature
  17. customThe obtained particles are dialyzed in water

Sources & evidence

ORD record
ord-aa333acfac484d0b82bfbab45aa0b5b8
Source dataset
uspto-grants-2009_07
Patent number
US07560023B2

Linked notes

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