Hydroquinone → 1-(2-Cyanoethyl)-3-(2-vinyloxyethyl)-5,5-dimethylhydantoin

HRID 127669Notes

Reaction equation

HRID 127669 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[NH:8][C:7]1=[O:14])=[CH2:2].[C:15](#[N:18])[CH:16]=[CH2:17].C1(C=CC(O)=CC=1)O.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO.CN(C)C=O>[C:15]([CH2:16][CH2:17][N:8]1[C:9]([CH3:13])([CH3:12])[C:10](=[O:11])[N:6]([CH2:5][CH2:4][O:3][CH:1]=[CH2:2])[C:7]1=[O:14])#[N:18]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 30179645,5-Dimethyl-3-(2-(vinyloxy)ethyl)imidazolidine-2,4-dione

Product 1

HCID 202856311-(2-Cyanoethyl)-3-(2-vinyloxyethyl)-5,5-dimethylhydantoin

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 237.8 g (1.2 mols) of 3-(2-vinyloxyethyl)-5,5-dimethylhydantoin, prepared as described in Example 1, 79.6 g (1.2 mols+20% excess) of acrylonitrile, 0.5 g of hydroquinone, 2.4 ml of a 40% solution of benzyltrimethylammonium hydroxide in methanol and 360 ml of dimethylformamide is allowed to react for 27 hours at 81°-85° C. The solution is then concentrated on a rotary evaporator at 90° C. under vacuum from a waterpump and the residue is dried to constant weight at 90° C. and 13.3 Pa. 300.4 g (99.6% of theory) of a dark brown, crystalline crude product are obtained and are purified by distillation. 260.8 g (86.5% of theory) of a crystalline distillate boiling at 147°-150° C. are obtained. After recrystallisation from ether, the product melts at 54.8°-55.5° C.

Workup

  1. customprepared
  2. customto react for 27 hours at 81°-85° C
  3. concentrationThe solution is then concentrated on a rotary evaporator at 90° C. under vacuum from a waterpump
  4. customthe residue is dried to constant weight at 90° C.
  5. custom300.4 g (99.6% of theory) of a dark brown, crystalline crude product are obtained
  6. distillationare purified by distillation
  7. custom260.8 g (86.5% of theory) of a crystalline distillate boiling at 147°-150° C. are obtained
  8. customAfter recrystallisation from ether

Sources & evidence

ORD record
ord-9753f8fca6d3480b9272b0aa474c0594
Source dataset
uspto-grants-1981_03
Patent number
US04256867

Reaction notes

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