Tetrahydrofuran → HCID 131730183, compound

HRID 1810828Notes

Reaction equation

HRID 1810828 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([CH:7]=[CH2:8])=[O:6])[CH3:3].[C:9]([O:13][N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20])(=[O:12])[CH:10]=[CH2:11].C1COCC1>C1(C)C=CC=CC=1>[CH3:1][CH:2]([NH:4][C:5]([CH:7]=[CH2:8])=[O:6])[CH3:3].[C:9]([O:13][N:14]1[C:15](=[O:20])[CH2:16][CH2:17][C:18]1=[O:19])(=[O:12])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 16637N-IsopropylacrylamideHCID 1815082-Propenoic acid, 2,5-dioxo-1-pyrrolidinyl ester

Product 1

HCID 131730183HCID 131730183, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To NIPAM (10.06 g, 88.9 mmol) and N-acryloxysuccinimide (NAS) (380 mg, 2.2 mmol) under nitrogen was added inhibitor free THF (25 ml) and toluene (25 ml). Nitrogen was bubbled through the solution for 5 minutes. The stirred reaction mixture was heated at 50° C. and free radical initiator 1,1′-azobis(cyanocyclohexane) VAZO® 88 was added (30 mg, 0.12 mmol, 0.3% by wt). The reaction was heated to 71-73° C. over 15 minutes. The reaction was further heated at this temperature for 18 hours. After this time, the solution appeared more viscous. The reaction mixture was cooled to ambient and a TLC test indicated a small amount of monomer present. The polymer was precipitated by the addition of hexane (100 ml). The white polymer is filtered off and dried under vacuum (20 mbar) to yield p(NIPAM-NAS) copolymer. (10.01 g).

Workup

  1. customNitrogen was bubbled through the solution for 5 minutes
  2. customThe stirred reaction mixture
  3. temperatureThe reaction was heated to 71-73° C. over 15 minutes
  4. temperatureThe reaction was further heated at this temperature for 18 hours
  5. temperatureThe reaction mixture was cooled to ambient and a TLC test
  6. customThe polymer was precipitated by the addition of hexane (100 ml)
  7. filtrationThe white polymer is filtered off
  8. customdried under vacuum (20 mbar)

Sources & evidence

ORD record
ord-81c2597217d0421fa8be39d5d5178769
Source dataset
uspto-grants-2013_01
Patent number
US08362217B2

Reaction notes

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