Hydroquinone → Methacryloyl vinyl urea

HRID 1721542Notes

Reaction equation

HRID 1721542 reaction equation
N#N.Cl.[C:4]([O:9]CCN)(=O)[C:5]([CH3:7])=[CH2:6].C1(C=CC(O)=CC=1)O.C([N:23](CC)CC)C.[CH:28]([N:30]=[C:31]=[O:32])=[CH2:29]>C(Cl)(Cl)Cl>[C:4]([N:30]([CH:28]=[CH2:29])[C:31]([NH2:23])=[O:32])(=[O:9])[C:5]([CH3:7])=[CH2:6]

Participants

7

Reactant 5

HCID 785HydroquinoneHCID 947NitrogenHCID 8471TriethylamineHCID 75495Aminoethyl methacrylate hydrochlorideHCID 77094Vinyl isocyanate

Product 1

HCID 22412625Methacryloyl vinyl urea

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A 500 ml 3-necked round bottom flask equipped with a reflux condenser, a mechanical stirrer, a thermometer, a dropping funnel and an efficient N2 blanket, is charged with 2-aminoethyl methacrylate hydrochloride 41.4 g (0.25 mole), 50 mg of hydroquinone and 300 ml of chloroform. The contents are cooled to between 0 and 5 degrees C. and stirred. Through a dropping funnel 25.3 g (0.25 mole) of triethylamine and 13.3 g (0.25 mole) of vinyl isocyanate in 50 ml of chloroform are added into the reaction flask and maintained at between 0 and 5 degrees C. The temperature is allowed to rise to room temperature with the contents stirred constantly overnight, passed through a silica gel column and dried with magnesium sulfate. The contents are then evaporated under reduced pressure to give the named product.

Workup

  1. customA 500 ml 3-necked round bottom flask equipped with a reflux condenser, a mechanical stirrer
  2. temperatureThe contents are cooled to between 0 and 5 degrees C
  3. temperaturemaintained at between 0 and 5 degrees C
  4. customto rise to room temperature with the contents
  5. stirringstirred constantly overnight
  6. dry with materialdried with magnesium sulfate
  7. customThe contents are then evaporated under reduced pressure
  8. customto give the named product

Sources & evidence

ORD record
ord-19c512847d88477197fb5da10b32e1ea
Source dataset
uspto-grants-1996_04
Patent number
US05512205

Reaction notes

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