Methanol → N-(Butoxycarbonylethyl)Maleimide Styrene

HRID 263657Notes

Reaction equation

HRID 263657 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:17]=1.N([C:40]([O:42][CH2:43][CH3:44])=[O:41])=NC([O-])=O.CO>CN(C=O)C>[CH2:43]([O:42][C:40]([CH2:16][CH2:17][N:5]1[C:4](=[O:6])[CH:3]=[CH:2][C:1]1=[O:7])=[O:41])[CH2:44][CH2:8][CH3:9].[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 66643759Maleimide styreneHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 86751013N-(Butoxycarbonylethyl)Maleimide Styrene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of maleimide-styrene copolymer are dissolved in 25 ml of DMF, 3 g of triphenylphosphine and 1.8 ml of ethyl azodicarboxylate are added, and the mixture is stirred for 15 minutes, during which slight warming occurs. 1.5 ml of L-(-)-butyl lactate are then added, and the mixture is stirred at room temperature for 20 hours, giving a clear, red-brown solution, which is poured into 300 ml of methanol. A milky-white precipitation of the polymer is obtained. Since the substance has a tacky consistency, it is separated off by centrifugation. After repeated washing with methanol and centrifugation, the product is dried at 70° C. in a drying cabinet. Yield 2.5 g. The polymer exhibits a rotation value of [α]D20 =+6.7° in the DMF solution.

Workup

  1. temperatureslight warming
  2. stirringthe mixture is stirred at room temperature for 20 hours
  3. customgiving a clear, red-brown solution, which
  4. customA milky-white precipitation of the polymer
  5. customis obtained
  6. customis separated off by centrifugation
  7. washAfter repeated washing with methanol and centrifugation
  8. customthe product is dried at 70° C. in a drying cabinet
  9. customa rotation value of [α]D20 =+6.7°

Sources & evidence

ORD record
ord-5ae181e1de3a4fe1ac280fea4242498b
Source dataset
uspto-grants-1997_07
Patent number
US05644016

Reaction notes

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